Polysubstituted cyclopentanes

In the early 1990s, Smith and co-workers reported on the total synthesis of the antitumor antibiotic macrolactam (+)-hitachimycin 35 (Figure 12.1) using a Noyori three-component coupling to assemble the polysubstituted cyclopentane unit [24]. 

An intramolecular Michael reaction (catalyzed by 2C) following the oxidative dearomatization of 4-substituted phenols provides valuable octalones. A method involving two consecutive Michael reactions to form optically active polysubstituted cyclopentanes should be highly rated. 

SCHEME 6 Preparation of polysubstituted cyclopentanes in total syntheses performed by the Ley research group. ... 

SCHEME 22.14. Michael additions of aUylsulfones syntheses of polysubstituted cyclopentanes and of (5)-anatabine. 

Cyclopentane ring annulation by a 3 + 2 radical cycloaddition reaction of 3-alkenyl type radicals 68 and 69 to electron-deficient olefins like 70-71, represents a useful methodology for the construction of polysubstituted cyclic molecules 72, 73 etc.2-4,46-48 Cekovic and coworkers have exercised... 

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