Unified approach for the total aynthesis of Bis-THF C-15 acetogenins: a chloroenyne from laurencia majuscula, laurendecumenyne B and laurefurenynes A/B

TitleUnified approach for the total aynthesis of Bis-THF C-15 acetogenins: a chloroenyne from laurencia majuscula, laurendecumenyne B and laurefurenynes A/B
Publication TypeJournal Article
Year of Publication2021
AuthorsSenapati, S, Unmesh, NA, Shet, MN, Ahmad, I, Ajikumar, N, Ramana, CV
JournalSynthesis-Stuttgart
Date PublishedMAY
Type of ArticleArticle; Early Access
ISSN0039-7881
Keywordsbis-THF C-15 acetogenins, carbohydrate building block, relay-cross-metathesis, S(N)2 halogenation, Sharpless asymmetric dihydroxylation-cycloetherification
Abstract

A highly diastereoselective total synthesis of several bis-THF C-15 acetogenin natural products, chloroenyne from Laurencia majuscula, laurendecumenyne B, and laurefurenyries A/B, is reported. Additionally the synthesis of an advanced intermediate reported in the earlier total synthesis of (E/Z)-elatenynes (formal synthesis) is described. The salient features in the synthesis include epoxide opening, Birch reduction, Sharpless asymmetric dihydroxylation-cycloetherification, S(N)2 halogenation, and a relay cross metathesis.
DOI10.1055/a-1500-1407, Early Access Date = MAY 2021
Type of Journal (Indian or Foreign)

Foreign
Impact Factor (IF)

2.675
Divison category: 
Organic Chemistry

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