Total synthesis of (+/-)-kellermanoldione: stepwise cycloaddition of a functionalized diene and allenoate.
نویسندگان
چکیده
The total synthesis of the diterpene kellermanoldione 1 is reported. Stepwise [4 + 2] cycloaddition of the ketal diene 8 and the allenoate 3 afforded the exo adduct 10x as the major product. It was converted into 1 via six steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether.
منابع مشابه
Total synthesis of (+/-)-hedychilactone B: stepwise allenoate diene cycloaddition to prepare trimethyldecalin systems.
[reaction: see text] The total synthesis of the diterpene hedychilactone B 1 is reported. The exo adduct 4x, the major product of the stepwise [4+2] cycloaddition of the diene 2 and the allenoate 3, has been converted into 1 via 7 steps, among them a key nonconjugative hydrolysis of a gamma-methylene silyl enol ether and an E-selective olefination.
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ورودعنوان ژورنال:
- Organic letters
دوره 11 17 شماره
صفحات -
تاریخ انتشار 2009