Synthesis of the C1-C9 fragment of callipeltoside-A

F Velázquez; H F Olivo

doi:10.1021/ol006003y

Synthesis of the C1-C9 fragment of callipeltoside-A

Org Lett. 2000 Jun 29;2(13):1931-3. doi: 10.1021/ol006003y.

Authors

F Velázquez¹, H F Olivo

Affiliation

¹ Division of Medicinal and Natural Products Chemistry, College of Pharmacy, and The Center for Biocatalysis and Bioprocessing, The University of Iowa, Iowa City, Iowa 52242, USA.

PMID: 10891194
DOI: 10.1021/ol006003y

Abstract

[reaction: see text] The C1-C9 fragment of callipeltoside (17) was prepared in 12 steps and 7.2% overall yield from bicyclic lactone (+)-4. Key steps include a stereoselective epoxidation and further regiocontrolled nucleophilic opening of the oxirane ring to install two vicinal stereocenters (C5 and C6), and the use of bis(trimethylsilyl) peroxide and a catalytic amount of Sn(IV) chloride for the chemoselective Baeyer-Villiger oxidation of unsaturated cyclopentanone 15.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Biochemistry / methods*
Macrolides*

Substances

Anti-Bacterial Agents
Macrolides
callipeltoside A