N-Methoxy-N-acylnitrenium Ions:  Application to the Formal Synthesis of (±)-Desmethylamino FR901483

The formal synthesis of (±)-desmethylamino FR901483 (2) is described. Construction of the unique azatricyclic skeleton of 2 was accomplished by a sequence which involved (i) preparation of dienone 7 by an N-methoxy-N-acylnitrenium ion-induced spirocyclization, (ii) formation of 2-azabicyclo[3.3.1]no...

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Published in:Organic letters 2001-07, Vol.3 (15), p.2353-2356
Main Authors: Wardrop, Duncan J, Zhang, Wenming
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Bridged-Ring Compounds - chemistry
Immunosuppressive Agents - chemical synthesis
Organophosphorus Compounds - chemical synthesis
Spiro Compounds - chemistry
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creator Wardrop, Duncan J
Zhang, Wenming
description The formal synthesis of (±)-desmethylamino FR901483 (2) is described. Construction of the unique azatricyclic skeleton of 2 was accomplished by a sequence which involved (i) preparation of dienone 7 by an N-methoxy-N-acylnitrenium ion-induced spirocyclization, (ii) formation of 2-azabicyclo[3.3.1]nonane 5 by the 6-(π-exo)-exo-trig radical cyclization of 1,7-enyne 6, and (iii) installation of the C-5 p-methoxybenzyl side chain by Lewis acid-mediated alkylation of silyl enol ether 18.
doi_str_mv 10.1021/ol0161514
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subjects Aza Compounds - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Bridged-Ring Compounds - chemistry
Immunosuppressive Agents - chemical synthesis
Organophosphorus Compounds - chemical synthesis
Spiro Compounds - chemistry
title N-Methoxy-N-acylnitrenium Ions:  Application to the Formal Synthesis of (±)-Desmethylamino FR901483
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