Collective Total Synthesis of Four Ganoderma Meroterpenoids Based on an Intramolecular Aldol Strategy

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-24 DOI:10.1021/acs.orglett.4c04756

Yasuhiro Meguro, Mari Oyake, Masaru Enomoto, Shigefumi Kuwahara

引用次数: 0

Abstract

The total synthesis of four Ganoderma meroterpenoids (lingzhiol, sinensilactam A, lingzhilactone B, and applanatumol I) has been accomplished from a known olefinic lactone in much shorter steps (4–8 steps) and markedly improved overall yields (15–27%) compared to previous syntheses. The key steps are highly regio- and diastereoselective intramolecular aldol reactions to prepare bicyclic lactone intermediates and a decarboxylative radical cyclization to install the unique tetracyclic ring system of lingzhiol.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.