12 Bacilosarcin AおよびBの全合成(口頭発表の部)
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Bacilosarcins A (1) & B (2), potent plant seed germination inhibitors comparable to herbimycin A, were recently isolated from the culture broth of Bacillus subtilis TP-B0611 by Igarashi and co-workers. Their unique structures featuring a 3,4-dihydroisocoumarin ring system linked to unprecedented heterocyclic frameworks as well as the intriguing biological activity prompted us to embark on their total synthesis. In this symposium, we report the first enantioselective total synthesis of 1, 2, and a structurally-related cytotoxin (Sg17-1-4) Starting from a known ester (11), the right segment (14) was synthesized in 6 steps through Cordova's asymmetric epoxidation, Z-selective Horner-Emmons olefination and TEA-mediated hydroxylactonization. The segment (14) was condensed with the left segment (25) prepared via the Sharpless kinetic resolution, and deprotected to give 3. Selective hydrolysis of its 5-membered lactone ring gave AI-77-B (26), an antiulcerogenic substance. The total synthesis of 1 was accomplished by selective ammonolysis of the 5-membered lactone moiety of 3 followed by condensation with diacetyl. N-Alkylation of 3 was successfully achieved by treatment of 3 with acetoin in the presence of MgSO_4, and the product 30 obtained as an epimeric mixture was converted into 2・HCl (formed as a single diastereomer) or Sg17-1-4 (34, a cytotoxin) by ammonolysis or hydrolysis, respectively. We will discuss a plausible mechanism for the stereoconvergent formation of 2 from 30. Thus, the first total synthesis of 1 and 2 has been accomplished in 10 steps from 11.
- 2008-09-01
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