Synthesis of side chain truncated 3"-aldehyde, 3"-carboxylic acid, and 1"-aldehyde from nodulisporic acid A.
An efficient synthesis of the truncated 3"-aldehyde (3) from nodulisporic acid A (1) under mild conditions is described. Further oxidation of 3 to 3"-carboxylic acid (4) and its subsequent oxidative degradation produced 1"-aldehyde (5). These new derivatives are versatile intermediates for the preparation of new, side chain modified derivatives of nodulisporic acid A. [reaction: see text]
Chakravarty
Prasun K
PK
Department of Medicinal Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. prasun_chakravarty@merck.com
Tyagarajan
Sriram
S
Shih
Thomas L
TL
Salva
Steve
S
Snedden
Christine
C
Wyvratt
Matthew J
MJ
Fisher
Michael H
MH
Meinke
Peter T
PT
D000447:Aldehydes / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007211:Indoles / Q000737:chemistry*; D007306:Insecticides / Q000737:chemistry*; D010084:Oxidation-Reduction
D000447:Aldehydes; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D007211:Indoles; D007306:Insecticides; C110703:nodulisporic acid A