Formal synthesis of (-)-perhydrohistrionicotoxin via cyclic amino acid ester-enolate Claisen rearrangement and ring-closing metathesis.
[reaction: see text] We have successfully synthesized an advanced synthetic intermediate, hydroxy lactam 3, which has previously been converted to perhydrohistrionicotoxin. An important feature of this synthesis is the creation of stereogenic centers by using the cyclic amino acid ester-enolate Claisen rearrangement together with a ring-closing metathesis for azaspirocyclic skeleton construction.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Ko
Hyojin
H
Lee
Taeho
T
Kim
Deukjoon
D
D000438:Alcohols / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry*; D000598:Amino Acids, Cyclic / Q000737:chemistry*; D000664:Amphibian Venoms / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D007769:Lactams / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D000470:Alkaloids; D000598:Amino Acids, Cyclic; D000664:Amphibian Venoms; D001372:Aza Compounds; D004952:Esters; D007769:Lactams; C004792:perhydrohistrionicotoxin