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First total synthesis of (+)-apotrisporin E and (+)-apotrientriols A-B: a cyclization approach to apocarotenoids.

Authors
  • González-Delgado, José A
  • Arteaga, Jesús F
  • Herrador, M Mar
  • Barrero, Alejandro F
Type
Published Article
Journal
Organic & Biomolecular Chemistry
Publisher
The Royal Society of Chemistry
Publication Date
Sep 07, 2013
Volume
11
Issue
33
Pages
5404–5408
Identifiers
DOI: 10.1039/c3ob41226a
PMID: 23863958
Source
Medline
License
Unknown

Abstract

The first total synthesis of the natural apocarotenoids (+)-apotrisporin E (1) and (+)-apotrientriols A and B (2-3) has been accomplished. The structure, relative stereochemistry and the assignation of the absolute configuration have been confirmed. This is a fast and easy access to this family of natural products whose key steps are a diastereoselective cyclization and a HWE olefination to attach the dienic side chain. This work also opens the door to the synthesis of other apocarotenoids such as trisporols and trisporic acids.

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