Book ChapterDOI
From D -Camphor to the Taxanes. Highly Concise Rearrangement- Based Approaches to Taxusin and Taxol
Leo A. Paquette,Mangzhu Zhao,Francis J. Montgomery,Qingbei Zeng,Ting Zhong Wang,Steven W. Elmore,Keith D. Combrink,Hui-Ling Wang,Simon R. Bailey,Zhuang Su +9 more
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TLDR
The de novo acquisition of taxusin and taxol has been fueled in large part by the enchanted structural features of these molecules and the much heralded antitumor efficacy of 2, particularly in patients beset with refractory ovarian, breast, and lung cancers.Abstract:
Our involvement with the de novo acquisition of taxusin (1) and taxol (2) has been fueled in large part by the enchanting structural features of these molecules and the much heralded antitumor efficacy of 2, particularly in patients beset with refractory ovarian, breast, and lung cancers.1 In combination with the unusual mode of action of 2, which exhibits a remarkable capacity for stabilizing microtubule assembly and deterring cell division,2 the intrinsically exciting promise shown by taxol for benefiting human health has commanded unrivaled attention.read more
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Journal ArticleDOI
From D-Camphor to the Taxanes: Highly Concise Rearrangement-Based Approaches to Taxusin and Taxol
Leo A. Paquette,Mangzhu Zhao,Francis J. Montgomery,Qingbei Zeng,Ting Zhong Wang,Steven W. Elmore,Keith D. Combrink,Hui-Ling Wang,Simon R. Bailey,Zhuang Su +9 more
TL;DR: Taxusin and taxol as discussed by the authors have been shown to have a remarkable capacity for stabilizing microtubule assembly and deterring cell division, which has attracted unrivaled attention.
Journal ArticleDOI
Recyclization reactions of 8,10-dibromocamphor with Grignard and organolithium compounds
Ihor Verenka,Marian V. Gorichko +1 more
TL;DR: The relative spatial arrangement of substituents in the molecule of (1-methyl-2-methylenebicyclo[3.2]heptan-6-yl)diphenylmethanol was studied by NOESY experiments as mentioned in this paper.
References
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Journal ArticleDOI
Promotion of microtubule assembly in vitro by taxol
TL;DR: It is reported here that taxol acts as a promoter of calf brain microtubule assembly in vitro, in contrast to plant products such as colchicine and podophyllotoxin, which inhibit assembly.
Journal ArticleDOI
First total synthesis of taxol. 1. Functionalization of the B ring
Robert A. Holton,Carmen Somoza,Hyeong B Kim,Feng Liang,Ronald J Biediger,P. Douglas Boatman,Mitsuru Shindo,Chase Smith,Soekchan Kim +8 more
Journal ArticleDOI
Total Synthesis of Baccatin III and Taxol
Samuel J. Danishefsky, , a,b John J. Masters,c Wendy B. Young,e Lawrence B. Snyder,f Thomas V. Magee,g David K. Jung,h Richard C. A. Isaacs,William Bornmann,i Cheryl A. Alaimo,h and Craig A. Coburn,Martin J. Di Grandi i +10 more
TL;DR: In this paper, the Wieland−Miescher ketone was used as a matrix to provide the C and D rings of the targets and to provide functionality implements for joining this sector to an A ring precursor.
Journal ArticleDOI
The clinical pharmacology and use of antimicrotubule agents in cancer chemotherapeutics.
TL;DR: The taxanes, led by the prototypic agent taxol, are emerging as another very active class of antimicrotubule agents.