325740-73-6Relevant articles and documents
Total synthesis of 10-isocyano-4-cadinene and its stereoisomers and evaluations of antifouling activities
Nishikawa, Keisuke,Nakahara, Hiroshi,Shirokura, Yousuke,Nogata, Yasuyuki,Yoshimura, Erina,Umezawa, Taiki,Okino, Tatsufumi,Matsuda, Fuyuhiko
, p. 6558 - 6573 (2011/10/05)
The first enantioselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, and determination of its absolute stereochemistry were achieved. 10-Isocyano-4-cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, intermolecular Diels-Alder reaction and samarium diiodide induced Barbier-type cyclization were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined as (1S,6S,7R,10S) by comparison of the optical rotations between natural and synthetic samples. In addition, the authors successfully synthesized 10-epi- and di-1,6-epi-10-isocyano-4-cadinene through the same synthetic pathway. Antifouling activities against Balanus amphitrite with the cadinenes were also evaluated.
Total Synthesis of 10-lsocyano-4-cadinene and Determination of Its Absolute Configuration
Nishikawa, Keisuke,Nakahara, Hiroshi,Shirokura, Yousuke,Nogata, Yasuyuki,Yoshimura, Erina,Umezawa, Taiki,Okino, Tatsufumi,Matsuda, Fuyuhiko
supporting information; experimental part, p. 904 - 907 (2010/06/16)
Chemical Equation Presentation The first enantloselective total synthesis of 10-isocyano-4-cadinene, a marine sesquiterpene isolated from nudibranchs of the family Phyllidiidae, was achieved. The cadinene is expected to be a novel nontoxic antifouling agent. In the synthesis, an intermolecular Diels-Alder reaction and a Sml2-induced Barbier-type reaction were employed as key steps. The absolute configuration of 10-isocyano-4-cadinene was determined to be (1S, 6S, 7R, 10S) on the basis of the total synthesis. Antifouling activities against Balanus amphitrite with both enantiomers of 10-isocyano4-cadinene were also evaluated
A convergent synthesis approach towards CGP60536B, a non-peptide orally potent renin inhibitor, via an enantiomerically pure ketolactone intermediate
Rueger,Stutz,Goschke,Spindler,Maibaum
, p. 10085 - 10089 (2007/10/03)
We report a convergent synthesis of the potent orally active non-peptide renin inhibitor CGP60536B. The key reaction employs the coupling of the enantiopure Grignard species derived from chloride 13 with the diastereomerically pure γlactone 9b. The stereoselective reduction of the resulting ketone 14b has been thoroughly investigated. (C) 2000 Elsevier Science Ltd.
A convergent synthesis of the renin inhibitor CGP60536B
Sandham,Taylor,Carey,Fassler
, p. 10091 - 10094 (2007/10/03)
Pseudoephedrine serves as a dual purpose chiral auxiliary and protecting group in the synthesis of the novel orally active renin inhibitor CGP60536B. (C) 2000 Elsevier Science Ltd.
Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)-butyrolactone: A quest for a practical route to an important hydroxyethylene isostere chiron
Hanessian, Stephen,Abad-Grillo, Teresa,McNaughton-Smith, Grant
, p. 6281 - 6294 (2007/10/03)
Several approaches for the stereocontrolled introduction of a 2-propyl group into (4S)-hydroxymethyl-1,4-butyrolactone via cholate chemistry were investigated. A practical synthesis of the (2R)- and (2S)-isomers was developed.
