Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

to related objects

Abstract: Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation‐borylation reaction to attach the cyclopropyl‐containing side chain.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A ; volume:128 ; number:7 ; year:2016 ; pages:2544-2548 ; extent:5
Angewandte Chemie ; 128, Heft 7 (2016), 2544-2548 (gesamt 5)

Creator: Millán, Alba
Smith, James R.
Chen, Jack L.‐Y.
Aggarwal, Varinder K.

DOI: 10.1002/ange.201511140

URN: urn:nbn:de:101:1-2022101007060862511334

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Millán, Alba
Smith, James R.
Chen, Jack L.‐Y.
Aggarwal, Varinder K.

Other Objects (12)

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

The Catalytic Asymmetric Intermolecular Prins Reaction

The Catalytic Asymmetric Intermolecular Prins Reaction

A new intermediate in the Prins reaction

A new intermediate in the Prins reaction

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

Tandem Enantioselective Zinc-Promoted Reaction

Tandem Enantioselective Zinc-Promoted Reaction

INVESTIGATION OF THE REACTION OF PHENYLISOCYANATE WITH N-SUBSTITUTED 2-IMINOOXAZOLIDINES

INVESTIGATION OF THE REACTION OF PHENYLISOCYANATE WITH N-SUBSTITUTED 2-IMINOOXAZOLIDINES

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

Katja Prins, the uncanny valley

Bildband

Katja Prins, the uncanny valley

Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

The Catalytic Asymmetric Intermolecular Prins Reaction

The Catalytic Asymmetric Intermolecular Prins Reaction

A new intermediate in the Prins reaction

A new intermediate in the Prins reaction

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

Tandem Enantioselective Zinc-Promoted Reaction

Tandem Enantioselective Zinc-Promoted Reaction

INVESTIGATION OF THE REACTION OF PHENYLISOCYANATE WITH N-SUBSTITUTED 2-IMINOOXAZOLIDINES

INVESTIGATION OF THE REACTION OF PHENYLISOCYANATE WITH N-SUBSTITUTED 2-IMINOOXAZOLIDINES

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

Katja Prins, the uncanny valley

Bildband

Katja Prins, the uncanny valley

Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

The Catalytic Asymmetric Intermolecular Prins Reaction

The Catalytic Asymmetric Intermolecular Prins Reaction

A new intermediate in the Prins reaction

A new intermediate in the Prins reaction

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

Synthesis of Substituted Pyrido-oxazine through Tandem SN2 and SNAr Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

The Construction of Highly Substituted Piperidines via Dearomative Functionalization Reaction

Tandem Enantioselective Zinc-Promoted Reaction

Tandem Enantioselective Zinc-Promoted Reaction

INVESTIGATION OF THE REACTION OF PHENYLISOCYANATE WITH N-SUBSTITUTED 2-IMINOOXAZOLIDINES

INVESTIGATION OF THE REACTION OF PHENYLISOCYANATE WITH N-SUBSTITUTED 2-IMINOOXAZOLIDINES

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Triple Cascade Reaction Leading to Tetra-Substituted Cyclohexenes

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

Katja Prins, the uncanny valley

Bildband

Katja Prins, the uncanny valley

Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.