title: Synthesis of side chain truncated 3"-aldehyde, 3"-carboxylic acid, and 1"-aldehyde from nodulisporic acid A.
abstract: 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]
authors.affiliation: Department of Medicinal Chemistry, Merck Research Laboratories, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065-0900, USA. prasun_chakravarty@merck.com
authors.forename: Prasun K
authors.initials: PK
authors.lastname: Chakravarty
authors.forename: Sriram
authors.initials: S
authors.lastname: Tyagarajan
authors.forename: Thomas L
authors.initials: TL
authors.lastname: Shih
authors.forename: Steve
authors.initials: S
authors.lastname: Salva
authors.forename: Christine
authors.initials: C
authors.lastname: Snedden
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Wyvratt
authors.forename: Michael H
authors.initials: MH
authors.lastname: Fisher
authors.forename: Peter T
authors.initials: PT
authors.lastname: Meinke
mesh_terms: 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
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D007211:Indoles; D007306:Insecticides; C110703:nodulisporic acid A