Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A

Barry B SNIDER; Nha Huu VO; Steven V O'NEIL

doi:10.1021/jo9804700

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Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A

Journal article

Peer reviewed

Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A

Barry B SNIDER, Nha Huu VO and Steven V O'NEIL

Journal of organic chemistry, Vol.63(14), pp.4732-4740

07/01/1998

DOI: https://doi.org/10.1021/jo9804700

Abstract

Mixtures

Alcohols

Conformation

Oxidation

Enones

(±)-Allocyathin B2 (2) and (+)-erinacine A (4), the 1-β-d-xyloside of (+)-allocyathin B2, the first cyathin diterpenes to be prepared, have been synthesized using a carbonyl ene reaction of 14a to construct an appropriately functionalized seven-membered ring and palladium-catalyzed carbonylation of dienyl triflates 10 and 39 as key steps. The entire cyathin carbon skeleton is constructed in seven steps, and allocyathin B2 is synthesized in only 17 steps (>5% overall yield) from readily available enone 9.

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Title: Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A
Creators: Barry B SNIDER - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02254-9110
Nha Huu VO - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02254-9110
Steven V O'NEIL - Department of Chemistry, Brandeis University, Waltham, Massachusetts 02254-9110
Publication Details: Journal of organic chemistry, Vol.63(14), pp.4732-4740
Publisher: American Chemical Society
Identifiers: 9924012820401921
Academic Unit: Department of Chemistry
Language: English
Resource Type: Journal article

Synthesis of (±)-Allocyathin B2 and (+)-Erinacine A

Abstract

Metrics

Details

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