Synlett 2021; 32(08): 822-828
DOI: 10.1055/a-1344-8713
letter

Four-Step One-Pot Catalytic Asymmetric Synthesis of Polysubstituted Tricyclic Compounds: Lipase-Catalyzed Dynamic Kinetic Resolution Followed by an Intramolecular Diels–Alder Reaction

Izuru Tsuchimochi
a   Graduate School of Pharmaceutical Sciences, Osaka University,1-6, Yamadaoka, Suita, Osaka 565-0871, Japan
b   Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Shuhei Hori
a   Graduate School of Pharmaceutical Sciences, Osaka University,1-6, Yamadaoka, Suita, Osaka 565-0871, Japan
,
Yasuo Takeuchi
b   Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University, 1-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan
,
Masahiro Egi
c   Graduate Division of Nutritional and Environmental Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
,
Tomo-o Satoh
d   School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan
,
Kyohei Kanomata
a   Graduate School of Pharmaceutical Sciences, Osaka University,1-6, Yamadaoka, Suita, Osaka 565-0871, Japan
,
Takashi Ikawa
a   Graduate School of Pharmaceutical Sciences, Osaka University,1-6, Yamadaoka, Suita, Osaka 565-0871, Japan
,
Shuji Akai
a   Graduate School of Pharmaceutical Sciences, Osaka University,1-6, Yamadaoka, Suita, Osaka 565-0871, Japan
› Author Affiliations
This work was financially supported by the JSPS KAKENHI [18HO4411 (Middle Molecular Strategy) and 18H02556] and the Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED under grant number JP20am0101084.


Abstract

Starting from readily available tertiary alcohols, four different reactions (a 1,3-migration of a hydroxy group, kinetic resolution, racemization, and an intramolecular Diels–Alder reaction) took place under co-catalysis by lipase and oxovanadium compounds in a one-pot process to produce polysubstituted tricyclic carbon frameworks in high yields and with high enantioselectivities. The key to the success of this process was the discovery that a silyl group attached to the terminal carbon of the vinyl moiety completely controls the direction of hydroxy group migration

Supporting Information



Publication History

Received: 07 December 2020

Accepted after revision: 04 January 2021

Accepted Manuscript online:
04 January 2021

Article published online:
26 January 2021

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