TY - JOUR
T1 - Furans as Versatile Synthons
T2 - Total Syntheses of Caribenol A and Caribenol B
AU - Hao, Hong Dong
AU - Trauner, Dirk
N1 - Funding Information:
We thank the Deutsche Forschungsgemeinschaft (SFB 749) for financial support. Dr. Peter Mayer is acknowledged for X-ray analyses. We thank Felix Hartrampf, Giulio Volpin, Dr. Julius R. Reyes, and Dr. Bryan Matsuura (all LMU Munich) for helpful discussions during the preparation of this manuscript and Irina Albrecht for early contribution to the project.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/3/22
Y1 - 2017/3/22
N2 - Two complex norditerpenoids, caribenols A and B, were accessed from a common building block. Our synthesis of caribenol A features the diastereoselective formation of the seven-membered ring through a Friedel-Crafts triflation and a late-stage oxidation of a furan ring. The first synthesis of caribenol B was achieved using an intramolecular organocatalytic α-arylation. An unusual intramolecular aldol addition was developed for the assembly of its cyclopentenone moiety, and the challenging trans-diol moiety was installed through a selective nucleophilic addition to a hydroxy 1,2-diketone. Our overall synthetic strategy, which also resulted in a second-generation synthesis of amphilectolide, confirms the usefulness of furans as powerful nucleophiles and versatile synthons.
AB - Two complex norditerpenoids, caribenols A and B, were accessed from a common building block. Our synthesis of caribenol A features the diastereoselective formation of the seven-membered ring through a Friedel-Crafts triflation and a late-stage oxidation of a furan ring. The first synthesis of caribenol B was achieved using an intramolecular organocatalytic α-arylation. An unusual intramolecular aldol addition was developed for the assembly of its cyclopentenone moiety, and the challenging trans-diol moiety was installed through a selective nucleophilic addition to a hydroxy 1,2-diketone. Our overall synthetic strategy, which also resulted in a second-generation synthesis of amphilectolide, confirms the usefulness of furans as powerful nucleophiles and versatile synthons.
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U2 - 10.1021/jacs.7b00234
DO - 10.1021/jacs.7b00234
M3 - Article
C2 - 28218534
AN - SCOPUS:85016086254
SN - 0002-7863
VL - 139
SP - 4117
EP - 4122
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 11
ER -