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. 2005 Jul 21;7(15):3323-5.
doi: 10.1021/ol051184v.

Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition

Kevin M Peese  1 , David Y Gin
Affiliations

Enantioselective approach to the hetisine alkaloids. Synthesis of the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core via intramolecular dipolar cycloaddition

Kevin M Peese et al. Org Lett. .

Abstract

[structure: see text]. An efficient, enantioselective approach to the hetisine class of the C(20)-diterpenoid alkaloids is described. The strategy involves an intramolecular oxidopyridinium dipolar cycloaddition as the key transformation, in which simultaneous formation of the C5-C6 and C10-C20 bonds in the 3-methyl-1-aza-tricyclo[5.2.1.0(3,8)]decane core of the hetisine alkaloids is effected.

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Figures

Figure 1
Figure 1
Atisane and hetisine alkaloids.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Scheme 3
Scheme 3
Scheme 4
Scheme 4
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