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首页> 外文期刊>Chemistry: A European journal >Total syntheses of zaragozic acids A and C by a carbonyl ylide cycloaddition strategy
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Total syntheses of zaragozic acids A and C by a carbonyl ylide cycloaddition strategy

机译：通过羰基内酯环加成策略合成zaragozic酸A和C

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摘要

A carbonyl ylide cycloaddition approach to the squalene synthase inhibitors zaragozic acids A and C is described. The carbonyl ylide precursor 8 was synthesized starting from di-tert-butyl D-tartrate (47) via an eleven-step sequence involving the regioselective reduction of the mono-MPM (MPM -4-methoxybenzyl) ether 48 with LiBH4 and the diastereoselective addition of sodium tert-butyl diazoacetate to alpha-keto ester 10. The reaction of alpha-diazo ester 8 with 3-butyn-2-one (40) in the presence of a catalytic amount of [Rh-2(OAc)(4)] gave the desired cycloadduct 59 as a single diastereomer. The dihydroxylation of enone 59 followed by sequential transformations permitted the construction of the fully functionalized 2,8-dioxabicyclo [3.2.1]octane core 5. Alkene 79 derived from 5 serves as a common precursor to zaragozic acids A (1) and C (2), since the elongation of the C1 alkyl side chain can be attained by olefin cross-metathesis, especially under the influence of Blechert's catalyst (85).
机译：描述了对角鲨烯合酶抑制剂泽拉果酸A和C的羰基内酯环加成方法。由D-酒石酸二叔丁酯（47）开始的11个步骤的羰基化前体8的合成过程包括用LiBH4选择性地还原单MPM（MPM -4-甲氧基苄基）醚48和非对映选择性加成重氮乙酸叔丁酯钠制得α-酮酸酯10。在催化量的[Rh-2（OAc）（4）存在下，α-重氮酯8与3-丁炔-2-酮（40）反应〕得到所需的环加合物59，为单一的非对映异构体。烯酮59的二羟基化，随后进行连续转化，可以构建功能齐全的2,8-二氧杂双环[3.2.1]辛烷核5。衍生自5的烯烃79作为zaragozic酸A（1）和C（ 2），因为C 1烷基侧链的伸长可以通过烯烃交叉复分解获得，尤其是在Blechert's催化剂（85）的影响下。

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