Synthesis 2019; 51(21): 3981-3988
DOI: 10.1055/s-0039-1690620
paper
© Georg Thieme Verlag Stuttgart · New York

A Metathetic Approach to [5/5/6] Aza-Tricyclic Core of Dendrobine, Kopsanone, and Lycopalhine A Type of Alkaloids

Sambasivarao Kotha
,
Sunil Pulletikurti
We are thankful to the Science and Engineering Research Board (EMR/2015/002053), New Delhi and CSIR [02(0272)/16/EMR-II], New Delhi for financial support. SP thanks UGC, New Delhi for financial support and the award of a SRF.
Further Information

Publication History

Received: 18 July 2019

Accepted after revision: 07 August 2019

Publication Date:
13 September 2019 (online)

Abstract

A concise synthetic approach to [5/5/6] tricyclic pyrrolidine core of dendrobine is reported. This methodology relies on the construction of β-hydroxylactams by NaBH4-I2 reduction followed by reaction of allylsilane with the aid of Lewis acid to generate alkenyl lactams in good yields. Further, ring-opening metathesis (ROM) followed by ring-closing metathesis (RCM) were used to assemble the [5/5/6] aza-tricyclic skeleton of dendrobine. This short synthetic route has been expanded to assemble tricyclic [5/5/8] system with pentenylboronic acid.

Supporting Information

 
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