- Highly efficient synthesis of (+)-nimbiol and other podocarpanes derivatives from sclareol
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A new access to tricyclic diterpenes of podocarpane skeleton has been opened, in excellent overall yields, and an efficient synthesis of (+)-nimbiol from sclareol has been achieved. Georg Thieme Verlag Stuttgart.
- Marcos, Isidro S.,Beneitez, Alvaro,Casta?eda, Lourdes,Moro, Rosalina F.,Basabe, Pilar,Diez, David,Urones, Julio G.
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- Lateral lithiation in terpenes: Synthesis of (+)-ferruginol and (+)-sugiol
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This paper describes the use of (-)-sclareol in the synthesis of the tricyclic diterpenes of abietane skeleton, such as (+)-ferruginol and (+)-sugiol, using as key step the lateral lithiation of a dinorditerpene derivative.
- Marcos,Beneitez,Moro,Basabe,Díez,Urones
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- Facile access to optically active ring C aromatic diterpene derivatives from manool. Highly efficient syntheses of (+)-12-methyl-7-oxo-podocarpa-8,11,13-triene-13-carboxylic acid, (+)-13-methyl-7-oxopodocarpa-8,11,13-triene-12-carboxylic acid and (+)-nimbiol
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The extension of our recently developed strategy using the key intermediate 2, obtainable in two steps (52% overall yield) from manool 1, to the synthesis of naturally occurring ring C aromatic diterpene derivatives provides in three steps (+)-12-methyl-7-oxopodocarpa-8,11,13-triene-13-carboxylic acid 4b and its isomer 6b, and in seven steps (+)-nimbiol 11b, in good overall yields. This synthesis discloses that the structure 4b assigned to margolone isolated from Azadirachta indica A. Juss is incorrect and needs to be reinvestigated.
- Nakano, Tatsuhiko,Alonso, Randolph,Maillo, Maria Aracelis,Martin, Alfonso,Nunez, Ramona Avila
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p. 1423 - 1426
(2007/10/03)
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