A new synthesis of dehydromunduserone

Fukui, Kenji; Nakayama, Mitsuru; Harano, Tetsuya

doi:10.1007/bf02144152

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Cited by 9 publications

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“…This was followed by a report from the same group on the total synthesis of 1 , though in an unstated overall yield . Later on, other interesting but quite inefficient routes have also been reported . Despite limited biological activity, 1 captured our attention as a convenient target for demonstrating novel synthetic strategies, for development of general approaches to more complex rotenoids.…”

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confidence: 99%

Protected Cyanohydrins in the Synthesis of Rotenoids: (±)-Munduserone and (±)-cis-12a-Hydroxymunduserone

Granados-Covarrubias

Maldonado

2009

J. Org. Chem.

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Short synthetic routes to the natural products (+/-)-munduserone 1 and (+/-)-cis-12a-hydroxymunduserone 9 from protected cyanohydrin 5 and nitrochromene 4 are described. The key coupling reaction of 4 and 5 gave under inverse addition conditions 9 (28%) and 2b (21%), while under normal addition conditions, a mixture of 9 (20%), dehydromunduserone 10 (9%), and enone 2b (10%) was obtained. (+/-)-Munduserone 1 is easily obtained from both 2b and 9 by 10% methanolic HCl (86%) and Zn/AcOH (71%) treatments, respectively.

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confidence: 99%