Synlett 2023; 34(15): 1799-1803
DOI: 10.1055/a-2058-3385
letter

Oxa-di-π-methane Rearrangement of a Substrate Embodying the Platencin Core Provides the Decahydro-1H-cyclopenta[c]indene Framework Associated with Various Diterpenes and Certain Lycopodium Alkaloids

a   Guangdong Key Laboratory for Research and the Development of Natural Drugs, The Marine Biomedical Research Institute, Guangdong Medical University, Zhanjiang, Guangdong 524023, P. R. of China
b   Institute for Advanced and Applied Chemical Synthesis, Jinan University, Zhuhai, 519070, P. R. of China
,
Faiyaz Khan
c   Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia
,
Michael G. Gardiner
c   Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia
,
Ping Lan
b   Institute for Advanced and Applied Chemical Synthesis, Jinan University, Zhuhai, 519070, P. R. of China
,
Sebastian Young Ye
c   Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia
› Author Affiliations

This work was supported by the Guangdong Medical University and the Australian Research Council.


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Abstract

A chemoenzymatic approach to the title framework is reported. The reaction sequence starts with the whole-cell biotransformation of iodobenzene and the conversion of the resulting homochiral metabolite into a triene that engages in an intramolecular Diels–Alder reaction and so affording an adduct embodying the platencin core. Application of an oxa-di-π-methane rearrangement to a derivative of this core affords a cyclopropannulated form of the target framework; the latter is then obtained through a TMSI-mediated cleavage of the three-membered ring. A strategy for the assembly of the enantiomeric framework is also described.

Supporting Information



Publication History

Received: 10 February 2023

Accepted after revision: 20 March 2023

Accepted Manuscript online:
20 March 2023

Article published online:
17 May 2023

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