Regioselective Diels-Alder reactions. A synthesis of the left-hand portion of CC-1065

Kraus, George A.; Yue, Stephen; Sy, James

doi:10.1021/jo00202a029

Cited by 28 publications

(8 citation statements)

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“…An imaginative route to CPI disclosed by Kraus was based on a regioselective Diels−Alder reaction of an unsymmetrical 1,4-dialkyl-substituted diene with an iminoquinone to quickly access the requisite number of carbons in CPI followed by the cleavage of the resulting cyclohexene to introduce the differentiated fused 5-membered rings (Scheme ). Embodied in this approach was the demonstration that an allylic acetate can produce unusual and useful levels of regioselectivity in the key Diels−Alder reaction.…”

Section: Kraus Synthesismentioning

confidence: 99%

CC-1065 and the Duocarmycins: Synthetic Studies

et al. 1997

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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.

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Section: Kraus Synthesismentioning

confidence: 99%

CC-1065 and the Duocarmycins: Synthetic Studies

et al. 1997

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“…Most recently, KRAUS et al 15) reacted the diene (13) regioselectively with 2-acetoxypento-l,3-diene, in a DIELS-ALDER reaction, to produce 14. Necessary protecting group shuffling, ozonolysis and cyclization afforded 15 which was converted to 12 in an overall yield of 5 % from 13.…”

Section: Synthesis Of the "A" Subunitmentioning

confidence: 99%

The chemistry, mechanism of action and biological properties of CC-1065, a potent antitumor antibiotic.

1986

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“…A Plieninger indolization strategy has been used on three separate occasions to construct the highly functionalized indolic subunits of these compounds. Kraus' synthesis of the CC-1065 CPI pharmacophore (A, Scheme 28) 36 utilized a highly regioselective Diels-Alder reaction between quinone di-imine 101 and diene 102 in the preparation of indolization precursor 103 (55%, 25:1 in favor of desired regioisomer). Treatment with BBr 3 unveiled the free phenol, which was protected as the benzoyl ester and subjected to acidic conditions to yield dihydronaphthalene 104 in 79% yield.…”

Section: 5mentioning

confidence: 99%

Synthesis of Highly Substituted Indoles via Diels-Alder/Plieninger Indolization Sequence: Applications in Total Synthesis

Sapeta¹,

Lebold²,

Kerr³

2011

Synlett

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Regioselective Diels-Alder reactions. A synthesis of the left-hand portion of CC-1065

Abstract: Diene 2b reacted regioselectively with dienophiles. Adduct 6 was converted into the left-hand portion of CC-1065 in 10% overall yield.

Cited by 28 publications

References 1 publication

CC-1065 and the Duocarmycins: Synthetic Studies

CC-1065 and the Duocarmycins: Synthetic Studies

The chemistry, mechanism of action and biological properties of CC-1065, a potent antitumor antibiotic.

Synthesis of Highly Substituted Indoles via Diels-Alder/Plieninger Indolization Sequence: Applications in Total Synthesis

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