Journal ArticleDOI
Synthesis of a Calicheamicin Deoxyaglycone Model by an Intramolecular Acetylide Cyclization
Andrew S. Kende,Cynthia A. Smith +1 more
TLDR
In this article, the reaction of enediyne aldehyde 16 with LiN(SiMe 3 ) 2 leads to intramolecular acetylide cyclization to the epimeric carbinols 17 comprising a deoxyaglycone model for the calicheamicins.About:
This article is published in Tetrahedron Letters.The article was published on 1988-01-01. It has received 74 citations till now. The article focuses on the topics: Esperamicin & Acetylide.read more
Citations
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Kleider machen Leute: Heck-Reaktion im neuen Gewand†
Armin de Meijere,Frank E. Meyer +1 more
TL;DR: The Heck-Reaktion as discussed by the authors is an example of a reaktion-based substrate with unsymmetrisch mehrfach substituierten Reaktionspartnern.
Journal ArticleDOI
Calicheamicin gamma 1I and DNA: molecular recognition process responsible for site-specificity
TL;DR: It is proposed that the cutting specificity is due to a combination of the complementarity of the diyne-ene portion of the aglycone with DNA secondary structures and stabilization by association of the thiobenzoate-carbohydrate tail with the minor groove.
Journal ArticleDOI
Molecular design, chemical synthesis, and biological action of enediynes
References
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Journal ArticleDOI
The Substitution of Aryl Iodides with Cuprous Acetylides. A Synthesis of Tolanes and Heterocyclics1
R. D. Stephens,C. E. Castro +1 more
Journal ArticleDOI
Calicheamicin gamma 1I: an antitumor antibiotic that cleaves double-stranded DNA site specifically
TL;DR: It is proposed that the observed cleavage specificity is a result of a unique fit of the drug and DNA followed by the generation of a nondiffusible 1,4-dehydrobenzene--diradical species that initiates oxidative strand scission by hydrogen abstraction on the deoxyribose ring.
Journal ArticleDOI
Esperamicins, a novel class of potent antitumor antibiotics. 3. Structures of esperamicins A1, A2, and A1b
Jerzy Golik,George R. Dubay,Gary S. Groenewold,Hiroshi Kawaguchi,Masataka Konishi,Bala Krishnan,Hiroaki Ohkuma,Kyoichiro Saitoh,Terrence W. Doyle +8 more
Journal ArticleDOI
A convenient preparation of trans (or cis) -1-chloroalkenes from trans (or cis)-1,2-dichloroethylene: A new synthesis of the sex pheromone of lobesia botrana.
TL;DR: In this paper, a simple synthesis of (7E, 9Z)-dodecadien-1-yl acetate has been realized, which can be used to synthesize trans (or cis)-dichloroethylene.