John Howard Hutchinson

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.

Formation of a novel thiopyranoindole ring system

The novel thiopyran[2,3,4-c,d]indole ring system (e.g.3) has been prepared from a substituted indole by intramolecular cyclisation of a t-BuS group onto an allyl substituent. The reaction occurs in high yield under the influence of protic acids, Lewis acids or electrophiles (Br2, I2, Hg(OAc)2)

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.

5,6-Dehydrocamphor: a chiral intermediate in terpenoid synthesis

Anionic oxy-Cope rearrangements of alkoxides derived from 5,6-dehydrocamphor provide chiral products which have potential as intermediates in the enantiospecific synthesis of terpenoids.

Use of camphor in steroid synthesis: a new approach to optically active trans-hydrindane derivatives

Ring cleavage of 9,10-dibromocamphor leads to the construction of an optically active hydrindenone derivative which has potential as an intermediate in steroid synthesis.

Enantiospecific synthetic approach to C,D-ring system of steroids with functionalized side-chains

Diastereoselective alkylation of a chiral ester derived from camphor provides potentially useful intermediates for the synthesis of steroids with functionalized side-chains.