163630-06-6Relevant articles and documents
The first stereoselective and the total synthesis of Leiocarpin C and total synthesis of (+)-Goniodiol
Yadav,Premalatha,Harshavardhan,Subba Reddy
scheme or table, p. 6765 - 6767 (2009/04/11)
The synthesis of the styryl lactone Leiocarpin C has been achieved in a highly stereoselective manner using Jacobsen's kinetic resolution, Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation as key steps. This is the first total synthesis of Leiocarpin C, and thus establishes for the first time the absolute stereochemistry of this natural product.
Total synthesis and cytotoxicity of (+)- and (-)-goniodiol and 6-epi-goniodiol. Construction of α,β-unsaturated lactones by ring-closing metathesis
Nakashima, Katsuyuki,Kikuchi, Naoki,Shirayama, Daisuke,Miki, Takuo,Ando, Kazuhiro,Sono, Masakazu,Suzuki, Shinya,Kawase, Masaki,Kondoh, Masuo,Sato, Masao,Tori, Motoo
, p. 387 - 394 (2008/02/11)
(+)-Goniodiol, a potent and selective cytotoxin, and (-)-6-epi-goniodiol, as well as their enantiomers, have been synthesized starting from cinnamyl alcohol. The key steps of the synthesis were Sharpless asymmetric epoxidation and cyclization of an acrylate derivative using ring-closing metathesis reaction. The cytotoxicity of both enantiomers of goniodiol and 6-epi-goniodiol against HL-60 cells was examined.
A highly enantioselective total synthesis of (+)-goniodiol
Tate, Edward W.,Dixon, Darren J.,Ley, Steven V.
, p. 1698 - 1706 (2008/02/11)
A high-yielding enantioselective total synthesis of the bioactive styryllactone (+)-goniodiol has been realised, starting from readily available (S)-glycidol. A key step is an oxygen-to-carbon rearrangement of a silyl enol ether linked via an anomeric cen
A total synthesis of the styryllactone (+)-goniodiol from naphthalene
Banwell, Martin G.,Coster, Mark J.,Edwards, Alison J.,Karunaratne, Ochitha P.,Smith, Jason A.,Welling, Lee L.,Willis, Anthony C.
, p. 585 - 595 (2007/10/03)
The cytotoxic natural product (+)-goniodiol (1) has been prepared in twelve steps from the enantiomerically pure cis-dihydrocatechol (2), which is readily obtained by microbial oxidation of naphthalene. Elaboration of compound (2) involves an initial oxid
A chemoenzymatic synthesis of the styryllactone (+)-goniodiol from naphthalene
Banwell, Martin G.,Coster, Mark J.,Karunaratne, Ochitha P.,Smith, Jason A.
, p. 1622 - 1624 (2007/10/03)
The enantiomerically pure cis-1,2-diol 2, which is obtained by microbial oxidation of naphthalene, has been converted, via a sequence of reactions including oxidative C-C bond cleavage, decarbonylation and ring-closing metathesis steps, into the natural p
Stereoselective syntheses of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone via alkoxyallylboration and ring-closing metathesis
Ramachandran, P. Veeraraghavan,Chandra, J. Subash,Reddy, M. Venkat Ram
, p. 7547 - 7550 (2007/10/03)
A convenient synthesis of (+)-goniodiol, (-)-8-epigoniodiol, and (+)-9-deoxygoniopypyrone has been developed via asymmetric alkoxyallylboration and ring-closing metathesis pathways.
A total synthesis of (+)-Goniodiol using an anomeric oxygen-to-carbon rearrangement
Dixon, Darren J.,Ley, Steven V.,Tate, Edward W.
, p. 3125 - 3126 (2007/10/03)
A new route to (+)-Goniodiol 1, a potent and selective cytotoxin, is described, using a diastereoselective oxygen-to-carbon rearrangement of an anomerically linked silyl enol ether as the key step.
Total synthesis of the natural goniodiol-8-monoacetate from cinnamyl alcohol
Yang,Zhou
, p. 743 - 744 (2007/10/02)
The first total synthesis of goniodiol-8-monoacetate, using the Sharpless asymmetric epoxidation starting from cinnamyl alcohol in twelve steps with an overall yield of 7%, is achieved.
