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Synthesis of (±)-ramulosin via inverse type hetero-diels-alder reaction 1

✍ Scribed by Klaus Vogt; Richard R. Schmidt

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
822 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

Condensatiar of 4-formylbutanoates (4 thloacetone (5) pcwided the 1 -oxa-1,3-dlene 4Ji?l,Y,',',",,p,"ni1i which afforded in high yielding inverse type hetero-Dlels-Am& reactions vith vinyl ethers and ketene acetals the desired dihydropyran cycloadducts 78-c and lla-c, respectively. Ttx? target molecule (* I-rarmlosln 7 qae obtmew from compound8 118 and 7a inconvenie5t ctbemotransformations. an< diastereoselectlve three and 'Rlur ' 5 (ace compound s in Scheme 2 1. A seven step synthesis of the raceinatt van developed by Cordova and Snider. 16 Actlnobolln (AI van imlated frca Strmtoaycer Q rl~ewlrldl~ 17 and its structure determined by different groupe. 18 It has broad spectrum antibiotic and moderate antltumor activity. rt is a potential carioatatlc agent. l9 IL is l This paper 1s dedicated to Professor E.C. Taylor on the occarlon of his 65 th birthday. K. Voor and R. R. SCWWT rochromatt (EC) on aluminum oxide in benzene in presence of molecular sieves 28 to yield ths b-iactone (~1-2 which by treatment with potassium tert.-butoxide in tetrahydrofuran nas readily cyelised to the destred ramul;;in (%)-A; its structure was assigned by comparison with published physical data.

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