TOTAL SYNTHESIS OF 11-DEOXYDAUNOMYCINONE
TOTAL SYNTHESIS OF 11-DEOXYDAUNOMYCINONE
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DOI：
10.1021/ja00355a028
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发表时间：
1983-01-01
影响因子：
15
通讯作者：
MAL, D
中科院分区：
文献类型：
--
作者：
HAUSER, FM;MAL, D
本文报道了11-脱氧道诺霉素酮（2a）的区域专一性合成。合成的关键要素是使用双环辛烯醇3a作为乙酰基取代的萘酮6的前体，所述乙酰基取代的萘酮6用作2a的A和B环的合成子。6与甲氧基（苯磺酰基）异苯并呋喃酮7的阴离子缩合，区域特异性地提供四环产物8，其在单一步骤中转化为四氢萘并烯酮9。9的八步制备以20%的总收率实现。
An efficient regiospecific synthesis of 11-deoxydaunomycinone (2a) is described. Key elements of the synthesis were the use of bicyclooctenol 3a as a precursor to the acetyl-substituted naphthalenone 6 which served as a synthon for the A and B rings of 2a. Condensation of 6 with the anion of the methoxy (phenylsulfonyl) isobenzofuranone 7 regiospecifically furnished the tetracyclic product 8, which was transformed to the tetrahydronaphthacenone 9 in a single step. The eight-step preparation of 9 was achieved in 20% overall yield.