EFFICIENT REGIOCONTROLLED SYNTHESIS OF SARKOMYCIN AND HOMOSARKOMYCIN
EFFICIENT REGIOCONTROLLED SYNTHESIS OF SARKOMYCIN AND HOMOSARKOMYCIN
复制标题
沙科霉素和高沙科霉素的高效区域控制合成
DOI：
10.1002/chin.198303371
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发表时间：
1982
期刊：
影响因子：
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通讯作者：
Amos B. Smith
中科院分区：
文献类型：
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作者：
B. Wexler;B. H. Toder;G. Minaskanian;Amos B. Smith
(3)Asahi，K.；Nagatsu，J.；Suzuki，S.J.Antiobiot。1966，A19,195。题名/责任者：Reashi，S.Agrie.比奥尔。化学。1970年，34325年。题名/责任者：Asahi，K.；Sakurai，T.；Imura，Y。1980、44、2257年。其合成见：Boschelli，D.；Smith，AB，Ill四面体Lett。1981年、22日、3733年。自1953年首次分离合成靶点并在1955.6‘7年阐明其结构以来，已发表的这种抗肿瘤药物的路线基本上是非区域控制的。8事实上，只有马克思和米纳斯卡恩最近的合成(1979)，9 Boeckman及其合作者的优雅的手性方法(1980)，10和Tsuji和Kobayashi的钯催化的环化路线(1981)，11实际上是区域控制的。然而，这些序列中的每一个都有长度的缺点(大约9或10步)。结合我们对环戊烷类抗生素的持续兴趣，我们高兴地在这里记录了肉霉素(1)及其同系物高肉霉素(2)的合成。12这两种合成序列都是短的、有效的和区域控制的；此外，两者都利用了现成的-(羟甲基)环戊酮(6)或其直接前体缩酮
(3) Asahi, K.; Nagatsu, J.; Suzuki, S. J. Antiobiot. 1966, A19, 195. Asahi, K.; Suzuki, S. Agrie. Biol. Chem. 1970, 34,325. Asahi, K.; Sakurai, T.; Imura, Y. Ibid. 1980, 44, 2257. For the synthesis see: Boschelli, D.; Smith, AB, Ill Tetrahedron Lett. 1981, 22, 3733. synthetic target since its initial isolation in 1953s and structural elucidation in 1955.6’7 By and large, however, published routes to this antitumor agenthave been non-regiocontrolled. 8 Indeed, only the very recent synthesis by Marx and Minaskanian (1979), 9 the elegant chiral ap-proach of Boeckman and collaborators (1980), 10 and the palladium-catalyzed cyclization route of Tsuji and Kobayashi (1981), 11 are in fact regiocontrolled. Each of these sequences, however, has the disadvantage of length (ca. 9 or 10 steps).In connection wiith our continuing interest in the cy-clopentanoid class of antibiotics, we are pleased to record here the synthesis of both sarkomycin (1) and its congener homosarkomycin (2). 12 Both synthetic sequences are short, efficient, and regiocontrolled; furthermore, both take advantage of the ready availability of «-(hydroxy-methyl) cyclopentenone (6) or its immediate precursor ketal