Chemo, regio, and stereoselective synthesis of a lipoarabinomannan from Mycobacterium tuberculosis using arabino and manno n-pentenylorthoesters

CARB 15

Bert Fraser-Reid, dglucose@aol.com, K N Jayaprakash, and Jun Lu. NPG Research Institute Inc, Centennial Campus, NC State Univesity, 840 Main Campus Dr, Ste 3540, Raleigh, NC 27606
The accompanying sketch (Turnbull et al. Angew. Chem. Int. Ed. Engl. 2004, 43I, 3918-3922) indicates the imposing complexity of the Lipoarabinomannan (LAM) component of M. tuberculosis cell wall, which has been described by Brennan as “an absolute treasure-house of unusual compounds” (Rouhi, C&EN, May 17, 1999, p 56). The cell wall's function, as the seat of the parasite's impregnability, has been the source of awe for over 120 years, a situation which is bound to continue in light of the world wide resurgence of tuberculosis, and its dreaded synergy with AIDS. A synthesis of LAM that relied on protecting group deployments would present a logistical nightmare. However, by judicious coupling of Donor/Acceptor “Match” with lanthanide salt induced control, a 23-unit construct has been assembled with chemo, regio and stereoselectivity from, ultimately, two n-pentenylorthoester sources.

 

Hudson Award Symposium
8:30 AM-12:00 PM, Monday, 14 March 2005 San Diego Marriott -- San Diego A, Oral

Division of Carbohydrate Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005