Total synthesis of twelve membered resorcyclic acid lactones, (R)-penicimenolide A, (R)-resorcyclide and (R)-dihydroresorcyclide

TitleTotal synthesis of twelve membered resorcyclic acid lactones, (R)-penicimenolide A, (R)-resorcyclide and (R)-dihydroresorcyclide
Publication TypeJournal Article
Year of Publication2021
AuthorsDas, P, D. Reddy, S
JournalTetrahedron
Volume85
Pagination132059
Date PublishedAPR
Type of ArticleArticle
ISSN0040-4020
KeywordsMacrocycle, Natural product, organic synthesis, Total synthesis
Abstract

Resorcyclic Acid Lactones or RALs are a class of fungal secondary polyketides isolated from a variety of fungal strains like Lasiodiplodia theobromae, Penicillium sp., Syncephalastrum racemosum etc. This class of macrocyclic lactones are found to exhibit a broad spectrum of biological activities and are of significant synthetic importance. Herein, we report the first total synthesis of (R)-penicimenolide A, twelve membered RAL (RAL12) isolated from Penicillium sp. (NO. SYP-F-7919). Besides, we also report the total synthesis of two other members, namely, (R)-trans-resorcyclide and (R)-dihydroresorcyclide. In the course of synthesis, we have utilized ring closing metathesis (RCM) as the key step in constructing the core macrolactone scaffold. (C) 2021 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2021.132059
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.233

Divison category: 
Organic Chemistry

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