A New Method for the Construction of Macrolides Stereoselective Synthesis of (±)‐Phoracantholide J. Preliminary communication | Zendy

Petrzilka Martin | Zendy

Premium

A New Method for the Construction of Macrolides Stereoselective Synthesis of (±)‐Phoracantholide J. Preliminary communication

Author(s) -

Petrzilka Martin

Publication year - 1978

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19780610833

Subject(s) - chemistry , stereoselectivity , stereochemistry , claisen rearrangement , selenium , sequence (biology) , lactone , acetal , combinatorial chemistry , organic chemistry , catalysis , biochemistry

Starting from 5‐chloro‐2‐pentanone ( 1 ) the naturally occurring 10‐membered lactone phoracantholide J ( 8a ) has been synthesized as its racemate in a sequence of six steps ( Scheme 2 ). Salient features of the syntheis include an internal selenium assisted acetal formation ( 4→5 ) and a stereoselective Claisen rearrangement ( 6→7→8 ). This general synthetic strategy offers an alternative approach towards the construction of macrocyclic lactones.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research