Thomas Money

An enantiospecific synthesis of estrone

Efficient cleavage of the C(1)—C(2) bond in 9,10-dibromocamphor (3) provides a chiral intermediate (5) that can be used in a new enantiospecific synthesis of estrone.

Synthesis of (±)-campherenone, (±)-epicampherenone, (±)-β-santalene, (±)-epi-β-santalene, (±)-α-santalene, (±)-ylangocamphor, (±)-copacamphor, and (±)-sativene

The completion of part of a general synthetic route to sesquiterpene analogues of camphor, bornan-2-ol, camphene and tricyclene is illustrated by an alternative total synthesis of campherenone and epicampherenone [the epimeric 1,7-dimethyl-7-(4-methylpent-3-enyl)norbornan-2-ones], β-santalene and epi-β-santalene [2-methyl-3-methylene-2-(4-methylpent-3-enyl)norbornanes], α-santalene {1,7-dimethyl-7-(4-methylpent-3-enyl)tricyclo-[2.2.1.02,6]heptane}, and the perhydro-1,4-methanoindene derivatives copacamphor, ylangocamphor, and sativene.

A stereospecific synthetic route to campherenone, campherenol, epicampherenone, β-santalene, epi-β-santalene, ylangocamphor, copacamphor, sativene, and copacamphene

A simple and efficient synthetic route to either enantiomeric form of campherenone and epicampherenone [the epimeric 1,7-dimethyl-7-(4-methylpent-3-enyl)norbornan-2-ones], β-santalene and epi-β-santalene [2-methyl-3-methylene-2-(4-methylpent-3-enyl)norbornanes], and the perhydro-1,4-methanoindene derivatives copacamphor, copacamphene, ylagocamphor, and sativene is described. The simplicity of the synthetic route is due to the application of a general synthetic plan and the development of a new process for effecting direct 8-substitution of camphor.

Enantiospecific synthesis of estrone

Efficient cleavage of the C(1)—C(2) bond in 9,10-dibromocamphor (3) provides a chiral intermediate (5) that can be used in a new enantiospecific synthesis of estrone.

Synthesis of (±)-camphor

An alternative proposal for the biosynthesis of the bornane series of bicyclic monoterpenes forms the basis of a new synthesis of camphor from p-menth-8-en-2-one (dihydrocarvone).

A formal, enantiospecific synthesis of pseudoguaianolides

Abstract The preparation of ketal-enone ( 3 ) and hydroxy-ketones ( 1a ), ( 16 ), and ( 4a ), from (−)-camphor ( 6 ) represents a formal enantiospecific synthesis of (+)-carpesiolin, (+)-confertin, (−)-damsin, (−)-helenalin, (+)-bigelovin, (+)-mexicanin I, and (+)-linifolin A.

An enantiospecific synthesis of 4-methylcamphor

Abstract Treatment of (−)-2-methylenebornane ( 7 ), derived from (+)-camphor (1), with 45% HBr /HOAc results in Wagner-Meerwein rearrangement and formation of 4-methylisobornyl bromide ( 17 ) in 80–90% yield. The enantiopurity of ( 17 ) was determined by conversion to (+)-4-methylisoborneol ( 5 ) and (−)-4-methylcamphor ( 3 ).

Synthesis and absolute configuration of the terpenes (–)-campherenone,(+)-epicampherenone, (–)-β-santalene, and (+)-epi-β-santalene

Biosynthetic considerations prompted synthetic studies which have resulted in reassignment of absolute configuration to (–)-campherenone and have established the absolute configuration of (+)-epicampherenone, (–)-β-santalene, and (+)-epi-β-santalene.

Microbiological hydroxylation of (+)- and (−)-bornyl acetate with Helminthosporium sativum and Fusarium culmorum.

Abstract The regiospecificity of hydroxylation of (+)- and (−)-bornyl acetateby cultures of Helminthosporium sativum and Fusarium culmorum has been determined.

Synthesis, absolute configuration, and photocyclisation of the sesquiterpene (–)-cryptomerion

The absolute configuration of cryptomerion has been established by synthesis from (–)-carvone and the conversion of cryptomerion into photocryptomerion is reported.