Format

Send to

Choose Destination
Org Lett. 2011 Jan 7;13(1):118-21. doi: 10.1021/ol102652t. Epub 2010 Dec 7.

A diastereoselective formal synthesis of berkelic acid.

Author information

1
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, California 93106-9510, United States.

Abstract

A formal synthesis of berkelic acid is reported. The strategy employs the combination of a chiral exocyclic enol ether and an achiral isochromanone to afford the chroman spiroketal core via a base-triggered generation and cycloaddition of an o-quinone methide intermediate. Other key steps include equilibration of the spiroketal, intramolecular benzylic oxidation, and lactone addition/hemiketal reduction; all occur with good diastereoselectivity.

PMID:
21138313
PMCID:
PMC3107127
DOI:
10.1021/ol102652t
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center