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Studies towards the total synthesis of novel dolabellane-type diterpenoids: construction of the 5,11-fused bicyclic framework

✍ Scribed by Goverdhan Mehta; Jayant D. Umarye


Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
137 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis


An oxy-Cope protocol has been grafted on to a previously crafted hydroazulenic system to provide a facile entry into the 5,11-fused bicyclic skeleton present in the novel neodolabellane diterpenoids. Formation of a novel tricyclic diterpenoid framework, generated through a transannular cyclization in the 11-membered ring present in the neodolabellane skeleton and embodying a bridged cycloheptatriene moiety, has also been encountered.


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The synthesis of the tetracyclic core present in the novel marine diterpenoid havellockate 1 has been accomplished from the readily available endo-dicyclopentadienone-10-ethylene ketal 3 as a prelude to the projected total synthesis of the natural product.