57714-93-9Relevant academic research and scientific papers
Diastereoselective route to the tetrahydropyranoid core of the polyketide herbicide herboxidiene
Banwell, Martin G.,Bui, Chinh T.,Simpson, Gregory W.,Watson, Keith G.
, p. 723 - 724 (1996)
Nerol 15 is readily converted, via initial asymmetric epoxidation, into compound 2 which contains the tetrahydropyranoid core of herboxidiene 1, a potent phytotoxic compound isolated from Streptomyces sp. A7847.
Diastereoselective synthesis of the tetrahydropyranoid core of the polyketide herbicide herboxidiene and model studies pertaining to attachment of the side-chain
Banwell, Martin G.,Bui, Chinh T.,Simpson, Gregory W.
, p. 791 - 799 (2007/10/03)
A diastereoselective synthesis of compound 2, which embodies the tetrahydropyranyl core of the polyketide herbicide herboxidiene (1), has been developed using asymmetric epoxidation of nerol as the initial step. Ketone 2 has been elaborated to phosphine oxide 24 which engages in a Horner-Wittig reaction with nonanal to give the E,E-diene 27, an analogue of herboxidiene. However, unlike compound 1, congeners 2 and 27 are not phytotoxic.
CONVENIENT SYNTHESIS OF CHIRAL EPOXYISOPRENOIDS BY YEAST REDUCTION
Kodama, Mitsuaki,Minami, Hiroyuki,Mima, Yukiko,Fukuyama, Yoshiyasu
, p. 4025 - 4026 (2007/10/02)
The terminal double bond of acyclic isoprenoids was converted into chiral epoxide in high optical yield by using asymmetric reduction of α-ketol with baker's yeast.
