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Studies toward the Synthesis of (−)‐Zampanolide: Preparation of the Macrocyclic Core
Author(s) -
Troast Dawn M.,
Yuan Jiayi,
Porco John A.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800247
Subject(s) - chemistry , aldol reaction , stille reaction , intramolecular force , silylation , methylene , pyran , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
Studies towards the synthesis of the macrocyclic core of (−)‐zampanolide are reported. The synthetic approach features a one‐pot reduction/vinylogous aldol reaction for construction of the C‐15–C‐20 fragment, an intramolecular silyl‐modified Sakurai (ISMS) reaction for construction of the 2,6‐ cis ‐disubstituted exo ‐methylene pyran subunit, and use of an sp 2 ‐ sp 3 Stille reaction for macrocyclization.