Total synthesis of rapamycin

KC Nicolaou, TK Chakraborty… - Journal of the …, 1993 - ACS Publications
Rapamycin (l)* 1· 2 is a novel, naturally occurring substance, with potent antibiotic, cytotoxic,
and immunosuppressive activity. Isolated from Streptomyces hygroscopicus found in an …

Total synthesis of rapamycin

SV Ley, MN Tackett, ML Maddess… - … A European Journal, 2009 - Wiley Online Library
… ozonolysis in our avermectin B 1a total synthesis project28 influenced our efforts at cleaving
… highly valuable in our rapamycin synthesis program (Scheme 4). Synthesis of epoxide 6: In …

Total synthesis of rapamycin

KC Nicolaou, AD Piscopio, P Bertinato… - … A European Journal, 1995 - Wiley Online Library
Details of the total synthesis of rapamycin (1) are reported. The synthesis required the preparation
of intermediates 4 – 9 in nonracemic form; key coupling reactions included a chromium…

Total synthesis of rapamycin

ML Maddess, MN Tackett, H Watanabe… - Angewandte Chemie …, 2007 - Wiley Online Library
… the formation of the rapamycin macrocycle by employing a transannular catechol-templated
Dieckmann-like reaction that was used with success in our recent synthesis of the related …

Total synthesis of (-)-rapamycin using an Evans-Tishchenko fragment coupling

D Romo, SD Meyer, DD Johnson… - Journal of the American …, 1993 - ACS Publications
… in place of the ketone at C32 of rapamycin.6 We reasoned that the C32-(S')-… total synthesis
of rapamycin that follows from these considerations.8 Our reported synthesis of the rapamycin

Total synthesis of rapamycin via a novel titanium-mediated aldol macrocyclization reaction

CM Hayward, D Yohannes… - Journal of the American …, 1993 - ACS Publications
… The total synthesis of rapamycin was first reported by Nicolaou et … In the case of rapamycin,
we recently described investigations … Herein, we disclose the total synthesis of rapamycin

Total synthesis of rapamycin and demethoxyrapamycin

AB Smith III, SM Condon, JA McCauley… - Journal of the …, 1995 - ACS Publications
… Herein we report the application of the former strategem to the total syntheses of rapamycin
(1) and demethoxyrapamycin (2). This first successful route to 2 confirmed the proposed …

A Unified Total Synthesis of the Immunomodulators (−)-Rapamycin and (−)-27-Demethoxyrapamycin: Assembly of the Common C (1− 20) Perimeter and Final …

AB Smith, SM Condon, JA McCauley… - Journal of the …, 1997 - ACS Publications
… We have devised and executed a unified, highly convergent total synthesis of (−)-rapamycin
(1) and (−)-27-demethoxyrapamycin (2), confirming the latter structure. For rapamycin, the …

A Unified Total Synthesis of the Immunomodulators (−)-Rapamycin and (−)-27-Demethoxyrapamycin: Construction of the C (21− 42) Perimeters

AB Smith, SM Condon, JA McCauley… - Journal of the …, 1997 - ACS Publications
A total synthesis of the potent, naturally occurring immunomodulators (−)-rapamycin (1) and
(−)-27-demethoxyrapamycin (2) has been achieved via a unified, highly convergent …

[图书][B] Total synthesis of rapamycin

CM Hayward - 1994 - search.proquest.com
… Our goal was to synthesize rapamycin via application of the chemistry developed in these
laboratories from the … A total synthesis would allow access to analogues that might be potential …