Synthesis of aplyolide A, ichthyotoxic macrolide isolated from the skin ofthe marine mollusk Aplysia depilans

Citation
A. Spinella et al., Synthesis of aplyolide A, ichthyotoxic macrolide isolated from the skin ofthe marine mollusk Aplysia depilans, SYNLETT, (12), 2001, pp. 1971-1973
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
2001
Pages
1971 - 1973
Database
ISI
SICI code
0936-5214(200112):12<1971:SOAAIM>2.0.ZU;2-A
Abstract
A convergent pathway is described for the synthesis of (S)-aplyolide A (1) using ethyl (S)-lactate as chiral source. Key steps, of the synthesis are t wo couplings between copper(T) alkynides and propargylic halides for the fo rmation of skipped diyne systems and were performed with an improved proced ure based on the use of cesium carbonate as base for alkynide preparation.