TY - JOUR
T1 - Formal Syntheses of (-)-Lepadiformines A, C, and (-)-Fasicularin
AU - Takashima, Katsuki
AU - Hayakawa, Daichi
AU - Gouda, Hiroaki
AU - Toyooka, Naoki
N1 - Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/5/3
Y1 - 2019/5/3
N2 - Marine tricyclic alkaloids lepadiformine and fasicularin, with a unique perhydropyrrolo[2,1-j]quinoline or perhydropyrido[2,1-j]quinoline framework, were synthesized starting from the B ring of the tricyclic system. This approach includes a highly stereocontrolled diallylation of a cyclic enaminoester and subsequent ring-closing metathesis to construct the A/B ring system, which was transformed into key lactams 32 and 33, and amino alcohol 37. Thus, we achieved formal syntheses of (-)-lepadiformines A, C, and (-)-fasicularin in a divergent manner.
AB - Marine tricyclic alkaloids lepadiformine and fasicularin, with a unique perhydropyrrolo[2,1-j]quinoline or perhydropyrido[2,1-j]quinoline framework, were synthesized starting from the B ring of the tricyclic system. This approach includes a highly stereocontrolled diallylation of a cyclic enaminoester and subsequent ring-closing metathesis to construct the A/B ring system, which was transformed into key lactams 32 and 33, and amino alcohol 37. Thus, we achieved formal syntheses of (-)-lepadiformines A, C, and (-)-fasicularin in a divergent manner.
UR - http://www.scopus.com/inward/record.url?scp=85065036478&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.9b00071
DO - 10.1021/acs.joc.9b00071
M3 - 学術論文
C2 - 30943035
AN - SCOPUS:85065036478
SN - 0022-3263
VL - 84
SP - 5222
EP - 5229
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -