Synthesis of the phosphodiesterase inhibitors PDE-I and PDE-II

Bolton, R.; Moody, Christopher J.; Rees, Charles W.; Tojo, Gabriel

doi:10.1039/c39850001775

Cited by 16 publications

(4 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Independent methanolysis of the separated diastereomers provided enantiomerically pure intermediates. Conversion of the primary alcohol to the chloride and acid-catalyzed deprotection followed by coupling of the unstable indoline hydrochloride with 5,6,7-trimethoxyindole-2-carboxylic acid , provided the enantiomerically pure penultimate intermediates. Final Winstein spirocyclization completed the synthesis of (+)-and ent -(−)-duocarmycin SA.…”

Section: Duocarmycinsmentioning

confidence: 99%

CC-1065 and the Duocarmycins: Synthetic Studies

et al. 1997

View full text Add to dashboard Cite

Born August 22, 1953, Dale L. Boger (seated) received his B.Sc. in chemistry from the University of Kansas (1975) and Ph.D. in chemistry from Harvard University (1980). Immediately following graduate school, he returned to the University of Kansas as a member of the faculty in the Department of Medicinal Chemistry (1979Chemistry ( −1985, moved to the Department of Chemistry at Purdue University (1985University ( −1991, and joined the faculty at The Scripps Research Institute (1991 to present) as the Richard and Alice Cramer Professor of Chemistry. His research interests span the fields of organic and bioorganic chemistry and include the development of synthetic methodology, the total synthesis of natural products, heterocyclic chemistry, bioorganic chemistry, medicinal chemistry, the study of DNA−agent and protein−ligand interactions, and antitumor agents.Christopher W. Boyce (standing left) was born January 30, 1972, and grew up in Richmond, MA. Following a year abroad at the Swiss Federal Institute (ETH-Zurich), he received his B.Sc. in chemistry from Rensselaer Polytechnic Institute (1994, summa cum laude). He is currently pursuing a Ph.D. under the direction of Professor Dale L. Boger where he is addressing the synthesis and evaluation of potent DNA alkylation agents related to the CC-1065 and duocarmycin families. Robert M. Garbaccio (standing right) was born on January 20, 1972, and grew up in Old Tappan, NJ. He received his B.A. in chemistry and graduated summa cum laude from Boston University in 1994 where he conducted research in the laboratory of Professor James S. Panek. Presently, he is pursuing a Ph.D. in chemistry at The Scripps Research Institute under the guidance of Professor Dale L. Boger where he is addressing the synthesis and evaluation of potent DNA alkylating agents from the duocarmycin and mitomycin families of antitumor antibiotics. Joel A. Goldberg (standing center) was born June 17, 1972, and grew up in Bedford, NH. After receiving his B.Sc. from Tufts University he joined Professor Boger's laboratory at The Scripps Research Institute where he is pursuing his Ph.D. in Chemistry. His research concentrates on the synthesis and evaluation of potent alkylating agents related to CC-1065 and the duocarmycins.

show abstract

Section: Duocarmycinsmentioning

confidence: 99%

CC-1065 and the Duocarmycins: Synthetic Studies

et al. 1997

View full text Add to dashboard Cite

show abstract

“…It is noteworthy that preparation of the indolecarboxylic acid moiety involved once again a successful implementation of the copper-mediated aryl amination (Scheme ). Thus, the Horner−Wadsworth−Emmons reaction of aldehyde 15 with phosphonate 16 furnished the requisite amination precursor 17 with excellent stereocontrol.…”

mentioning

confidence: 99%

Total Synthesis of the Duocarmycins

et al. 2003

View full text Add to dashboard Cite

show abstract

“…it has become commonplace to instead remove the carboxyl function at the indole-2-position by decarbonylative procedures,® burdening any synthetic tree with additional steps. 6 In connection with our studies on microwaveaccelerated synthetic transformations,7 we reasoned that microwave-induced thermolysis of indole-2-carboxylate derivatives may allow decarboxylation to be accomplished with ease and now wish to report a successful protocol.…”

mentioning

confidence: 99%

Decarboxylation of indole-2-carboxylic acids: improved procedures

Jones¹,

Chapman²

1993

J. Org. Chem.

View full text Add to dashboard Cite

Of the many synthetic avenues to 2-unsubstituted indoles available, classical approaches including the Reissert,1 Fischer,2 and Rees-Moody3 routes require subsequent removal of the 2-carboxyl function. Several procedures have been reported to effect this problematic transformation with widely ranging degrees of efficiency.4 5" Problems encountered during the process usually stem from decomposition of the product under prolonged thermolysis conditions, and additional decomposition during purification of the crude product. For these reasons

show abstract

Synthesis of the phosphodiesterase inhibitors PDE-I and PDE-II

Cited by 16 publications

References 3 publications

CC-1065 and the Duocarmycins: Synthetic Studies

CC-1065 and the Duocarmycins: Synthetic Studies

Total Synthesis of the Duocarmycins

Decarboxylation of indole-2-carboxylic acids: improved procedures

Contact Info

Product

Resources

About