Formal total synthesis of (-)-lepadiformine.
[reaction: see text] A stereocontrolled approach to the preparation of the Weinreb intermediate 3 has been developed. The important features of this approach are the creation of stereogenic centers through a cyclic amino acid ester-enolate Claisen rearrangement and the use of ring-closing metathesis for the construction of the azaspirocyclic skeleton.
Lee
Minhee
M
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea.
Lee
Taeho
T
Kim
Eun-Young
EY
Ko
Hyojin
H
Kim
Deukjoon
D
Kim
Sanghee
S
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D003500:Cyclization; D015394:Molecular Structure; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry
D000470:Alkaloids; C431548:lepadiformine