2277-16-9Relevant articles and documents
Stereoselective synthesis of the C17–C29 fragment of amphidinolide N
Fujishima, Yuki,Ogura, Yusuke,Towada, Ryo,Enomoto, Masaru,Kuwahara, Shigefumi
, p. 5240 - 5242 (2016)
An enantio- and diastereoselective synthesis of the C17–C29 fragment of amphidinolide N, an extremely potent macrocyclic cytotoxin of marine origin, has been accomplished from a known olefinic ester by a 10-step sequence that involves a ring opening of a chiral epoxide with a dithiane derivative to construct the full carbon skeleton, a highly diastereoselective reduction of a β-hydroxy ketone intermediate to install the C21 asymmetric center, and a one-pot Sharpless AD/cyclization sequence to form a trans-substituted tetrahydrofuran ring system.
Easy access to aroma active unsaturated γ-lactones by addition of modified titanium homoenolate to aldehydes
Frerot, Eric,Bagnoud, Alain
experimental part, p. 4057 - 4061 (2011/10/31)
The homo-Reformatsky reaction, in which a metal homoenolate of an ester is added to an aldehyde, was adapted to produce γ-lactones from unsaturated, enolizable aldehydes. By use of titanium homoenolate, 11 different γ-lactones were synthesized in one step with moderate to good yields from readily available aldehydes. In particular, this procedure allowed the rapid preparation of a series of C12 unsaturated γ-lactones differing in the position and configuration of the double bond. These reference compounds will be used to identify previously unknown lactones in butter oil. The chromatographic, spectral, and sensory descriptions of the synthesized lactones are provided.
Synergistic sex pheromone components of white-spotted tussock moth, Orgyia thyellina
Gries, Gerhard,Clearwater, John,Gries, Regine,Khaskin, Grigori,King, Skip,Schaefer, Paul
, p. 1091 - 1104 (2007/10/03)
In 1996, the exotic white-spotted tussock moth (WSTM), Orgyia thyellina (Lepidoptera: Lymantriidae), was discovered in Auckland, New Zealand. Because establishment of WSTM would threaten New Zealand's orchard industry and international trade, eradication of WSTM with microbial insecticide was initiated. To monitor and complement eradication of WSTM by capture of male moths in pheromone-baited traps, pheromone components of female WSTM needed to be identified. Coupled gas chromatographic-electroantennographic detection analysis of pheromone gland extract revealed several compounds that elicited responses from male moth antennae. Mass spectra of the two most EAD-active compounds suggested, and comparative GC-MS of authentic standards confirmed, that they were (Z)-6-heneicosen-11-one (Z6-11-one) and (Z)-6-heneicosen-9- one, the latter termed here 'thyellinone.' In field experiments in Japan, Z6- 11-one plus thyellinone at a 100:5 ratio attracted WSTM males, whereas either ketone alone failed to attract a single male moth. Addition of further candidate pheromone components did not enhance attractiveness of the binary blend. Through the 1997-1998 summer, 45,000 commercial trap lures baited with 2000 μg of Z6-11-one and 100 μg of thyellinone were deployed in Auckland towards eradication of the residual WSTM population.
