A formal synthesis of antimalarial diterpenoid 7,20-diisocyanoadociane, isolated from marine sponge Adocia sp., was achieved. The authors synthesized Corey’s synthetic intermediate 2 for 7,20-diisocyanoadociane. This synthesis involves the synthesis of a perhydropyrene derivative using a sequential isomerization–intramolecular Diels–Alder reaction as the key step.
A Formal Synthesis of Antimalarial Diterpenoid 7,20-Diisocyanoadociane. -Corey's synthethic intermediate (V) for the synthesis of the title compound can be obtained by using a sequential isomerization-intramolecular Diels-Alder reaction as the key step, cf. (I)→(II). This is the first example of a sequential isomerization-intramolecular Diels-Alder reaction in the presence of a base. The isomers (II) can be separated after the deprotection of the Ph 3 C-group. -(MIYAOKA*, H.; OKUBO, Y.; MUROI, M.; MITOME, H.; KAWASHIMA, E.; Chem. Lett. 40 (2011) 3, 246-247, http://dx.doi.org/10.1246/cl.2011 Sch. Pharm., Univ. Pharm. Life Sci., Hachioji, Tokyo 192, Japan; Eng.) -C. Gebhardt
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