Divergent Asymmetric Total Synthesis of (−)‐Voacafricines A and B
Abstract: A divergent asymmetric total synthesis of voacafricines A and B, hexacyclic monoterpene indole alkaloids, has been accomplished featuring the following key steps: a) a catalyst‐controlled asymmetric Pictet–Spengler reaction of 6‐methoxytryptamine with a chiral α‐ketoester affording a 1,1‐disubstituted tetrahydro‐β‐carboline in excellent yield and diastereoselectivity; b) oxidative cleavage of a 3,5‐disubstituted cyclopentene furnishing a dialdehyde intermediate, which was effectively differentiated through spontaneous cyclization with the neighboring hydroxy and secondary amine functions; c) intramolecular nucleophilic addition of a tertiary amino nitrogen atom to the in situ generated oxonium species generating stereoselectively an unprecedented 8‐alkyl octahydro‐2H‐5,8‐methanofuro[2,3‐b]azepin‐8‐ium motif bearing five contiguous stereocenters. The synthesis confirmed the absolute configuration of these two natural products.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Divergent Asymmetric Total Synthesis of (−)‐Voacafricines A and B ; day:13 ; month:03 ; year:2023 ; extent:7
Angewandte Chemie / International edition. International edition ; (13.03.2023) (gesamt 7)
- Creator
- DOI
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10.1002/anie.202301517
- URN
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urn:nbn:de:101:1-2023031414114857613981
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
- 14.08.2025, 10:45 AM CEST
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Associated
- Andres, Rémi
- Wang, Qian
- Zhu, Jieping
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