• CAS Science Spotlight Home
• About
• What's New

Home   •   Spotlight  •  rlist1q04j  •  Most Requested Journal Articles 1Q04-Chemistry and Related (4)

Most Requested Journal Articles 1Q04-Chemistry and Related

Following is one of the journal articles most requested by researchers using CAS online services.

---

CAS indexed 42 chemical substances from this document. CAS subject entries for this document include: Peptides, preparation; Anti-AIDS agents; Asymmetric synthesis and induction; and 2 additional concepts.

CAPLUS COPYRIGHT 2004 ACS on STN

TITLE:	Total Synthesis of Anti-HIV Agent Chloropeptin I
AUTHOR(S):	Deng, Hongbo; Jung, Jae-Kyung; Liu, Tao; Kuntz, Kevin W.; Snapper, Marc L.; Hoveyda, Amir H.
CORPORATE SOURCE:	Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA
SOURCE:	Journal of the American Chemical Society (2003), 125(30), 9032-9034 CODEN: JACSAT; ISSN: 0002-7863
PUBLISHER:	American Chemical Society
LANGUAGE:	English

 

ABSTRACT:
A convergent diastereo- and enantioselective total synthesis of anti-HIV agent chloropeptin I (I) is reported. Important features of the total synthesis include: (1) the use of titanium-catalyzed cyanide addn. to imines to prep. a requisite amino acid moiety, (2) the discovery of the pos. effect of MeOH in the Cu-mediated biaryl ether formation to afford one of the two macrocyclic peptide moieties, and (3) the discovery of the pos. influence of collidine in the diastereoselective Pd-mediated cross-coupling to result in efficient formation of another macrocycle within this medicinally important mol. This key step is performed in the presence of four unprotected phenols, two of which reside on dichlorophenylglycines.

View full-text pdf document from the American Chemical Society, a participating ChemPort publisher.