Work

A Diastereoselective Formal Synthesis of Berkelic Acid

Year: 2010

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol102652t

Authors: Todd A. Wenderski, Maurice A. Marsini, Thomas R. R. Pettus

Institution: University of California, Santa Barbara

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G6704650334, The Synthesis and Application of Novel Aromatic Materials