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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.