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. 2010 Feb 5;75(3):933-6.
doi: 10.1021/jo902172r.

Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C

Stephen Philip Fearnley  1 , Charnsak Thongsornkleeb
Affiliations

Oxazolone cycloadducts as heterocyclic scaffolds for alkaloid construction: synthesis of (+/-)-2-epi-pumiliotoxin C

Stephen Philip Fearnley et al. J Org Chem. .

Abstract

Intramolecular Diels-Alder cycloaddition of N-substituted oxazolone triene I allows direct entry to the functionalized octahydroquinoline II. Further manipulation of this framework by stereo- and regioselective introduction of the 5-methyl substituent, followed by excision of the carbamate, yields (+/-)-2-epi-pumiliotoxin C.

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Figures

Figure 1
Figure 1
Representative decahydroquinoline targets
Scheme 1
Scheme 1
Oxazolone IMDA approach to 2-epi-pumiliotoxin C
Scheme 2
Scheme 2
Synthesis of triene precursor
Scheme 3
Scheme 3
Initial cycloaddition studies
Scheme 4
Scheme 4
Synthesis of (±)-2-epi-pumiliotoxin C
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