Organocatalytic tandem Morita–Baylis–Hillman–Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic indanone scaffold

Xiang Li; Lei Yang; Cheng Peng; Xin Xie; Hai-Jun Leng; Biao Wang; Zheng-Wei Tang; Gu He; Liang Ouyang; Wei Huang; Bo Han

doi:10.1039/C3CC44004D

Organocatalytic tandem Morita–Baylis–Hillman–Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic indanone scaffold†

Xiang Li,‡^a Lei Yang,‡^a Cheng Peng,*^ab Xin Xie,^a Hai-Jun Leng,^b Biao Wang,^b Zheng-Wei Tang,^b Gu He,^c Liang Ouyang,^c Wei Huang*^b and Bo Han*^a

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* Corresponding authors

^a State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine Resources, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China
E-mail: hanbo@cdutcm.edu.cn, pengchengchengdu@126.com
Fax: +86 28 61800234

^b School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, P. R. China
E-mail: huangwei@cdutcm.edu.cn
Fax: +86 28 61800231

^c State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041, P. R. China
Fax: +86 28 85503817

Abstract

A novel multicatalytic MBH–Michael tandem reaction has been developed for the asymmetric assembly of ninhydrin, nitroolefins and aldehydes into a structurally complex oxa-spirocyclic indanone backbone. Successive iodocyclization allowed us to convert these multifunctional allylic products into fused chiral natural product mimics.

Chemical Communications

Organocatalytic tandem Morita–Baylis–Hillman–Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic indanone scaffold†

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Organocatalytic tandem Morita–Baylis–Hillman–Michael reaction for asymmetric synthesis of a drug-like oxa-spirocyclic indanone scaffold

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