A. Martín scite author profile

~~ ~~On treatment with boron trifluoride-diethyl ether in benzene the epoxide (3b) of methyl (-) -kaur-9( 11 )en-19-oate (2c) yielded an aldehyde (5a). During the epoxidation of compound (2c) with mchloroperbenzoic acid it was observed that in the presence of N-nitrosomethylurea the expected epoxide (3b) was not obtained, but instead compound (4) was isolated. Detailed studies showed that epoxide (3b) is an intermediate for the formation of compound (4) from compound (2c), and aldehyde (5a) is also involved in its mechanistic pathway. Epoxidation of aldehyde (5a), followed by acid treatment, led to compound (4). On rupture with boron trifluoride-diethyl ether in acetic anhydride epoxide (3b) afforded acylal (5b) in good yield.(-) -Kaur-9( 1 1 ) -en-1 9-oic acid (2b) behaved similarly. On rupture with boron trifluoride-diethyl ether its epoxide (3a) gave also an aldehyde, (5c), while on treatment with boron trifluoride-diethyl ether in acetic anhydride it yielded acylal (5d).

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A facile access to optically active ring C aromatic diterpene derivatives. Highly efficient synthesis of (+)-12-methyl-7-oxopodocarpa-8,11,13-triene-13-carboxylic acid and (+)-13-methyl-7-oxopodocarpa-8,11,13-triene-12-carboxylic acid from manool

Nakano

Alonso

Maillo

et al. 1995

Tetrahedron Letters

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A. Martín

Synthesis, characterization and controlled release behaviour of adducts from chloroacetylated cellulose and α-naphthylacetic acid

Backbone rearrangements of methyl (-)-kaur-9(11)-en-19-oate and its epoxide: structures of two diterpenes of a new skeletal type

Synthesis of labda-8(17),13(14)-diene-15,16-olide and 15,16-epoxy-labda-8(17),13(16)-14-triene and their rearrangement to clerodane derivatives

A facile access to optically active ring C aromatic diterpene derivatives. Highly efficient synthesis of (+)-12-methyl-7-oxopodocarpa-8,11,13-triene-13-carboxylic acid and (+)-13-methyl-7-oxopodocarpa-8,11,13-triene-12-carboxylic acid from manool

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