A retro-Claisen approach to dolabriferol.
[reaction: see text] The protected precursor 30 to dolabriferol was generated by a DBU-induced, ester-forming, retro-Claisen process. The required linear carbon chain present in 22 was synthesized by a stereoselective lithium aldol reaction. The necessary aldehyde and ketone fragments were synthesized using stereocontrolled aldol reactions with the ethyl (S)-lactate derived ketone 13.
Lister
Troy
T
School of Chemistry, Physics and Earth Sciences, Flinders University, G. P. O. Box 2100, S.A. 5001, Australia.
Perkins
Michael V
MV
D000818:Animals; D001048:Aplysia / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D011714:Pyrans; C516274:dolabriferol