Total synthesis of furanocembranolides. 1. Stereocontrolled preparation of key heterocyclic building blocks and assembly of a complete seco-pseudopterane framework
Total synthesis of furanocembranolides. 1. Stereocontrolled preparation of key heterocyclic building blocks and assembly of a complete seco-pseudopterane framework
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呋喃西伯内酯的全合成。
DOI：
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发表时间：
1992
期刊：
影响因子：
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通讯作者：
C. Rayner
中科院分区：
文献类型：
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作者：
L. Paquette;A. Doherty;C. Rayner
提出了一种全合成伪蝶内酯及其相关伪蝶烷的反合成策略。该方案取决于早期制备合适的2,5-二官能化3-糠酸酯。为此，以2,3- o -异丙基- d -甘油醛和4（苯基硫）乙酸甲酯为原料，很容易地合成了对有用的底物21和24。接下来研究了这两种中间体转化为呋喃内酯27。控制立体化学的最佳方法是在三氟化硼催化下与3-甲酰丙酸甲酯缩合
A retrosynthetic strategy for the total synthesis of pseudopterolide and allied pseudopteranes is presented. This scheme is dependent upon early elaboration of suitable 2,5-difunctionalized 3-furoate esters. To this end, the pair of useful substrate 21 and 24 was readily synthesized from 2,3-O-isopropylidene-D-glyceraldehyde and methyl 4(phenylthio)acetoacetate. The conversion of both of these intermediates into furanolactone 27 was next studied. The best method for gaining suitable control of stereochemistry involved condensation of 24 with methyl 3-formylpropionate under conditions of boron trifluoride catalysis