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  • Synthesis of (+)-patulolide C via an asymmetric hydroformylation/macrocyclization cascade.

Synthesis of (+)-patulolide C via an asymmetric hydroformylation/macrocyclization cascade.

Organic letters (2012-02-07)
Roberto M Risi, Steven D Burke
PMID22304535
ABSTRACT

A highly atom-economical total synthesis of (+)-patulolide C has been accomplished in three steps from the known (2R)-8-nonyn-2-ol in 49% overall yield and 93% de. A Rh(I)-catalyzed asymmetric hydroformylation (AHF)/ intramolecular Wittig olefination cascade was utilized to set the C4-hydroxyl stereochemistry and E-olefin geometry as well as form the macrolactone.

MATERIALS
Product Number
Brand
Product Description
40327
Supelco
Vinyl acetate solution, certified reference material, 5000 μg/mL in acetonitrile
33-0390
Sigma-Aldrich
Vinyl acetate, CP
V1503
Sigma-Aldrich
Vinyl acetate, contains 3-20 ppm hydroquinone as inhibitor, ≥99%
48486
Supelco
Vinyl acetate, analytical standard
Y0000793
Vinyl acetate, European Pharmacopoeia (EP) Reference Standard