Volume 38, Issue 23 pp. 3537-3539
Communication

Total Synthesis of (+)-Deoxypyrrololine: A Potential Biochemical Marker for Diagnosis of Osteoporosis

Maciej Adamczyk

Maciej Adamczyk

Division Organic Chemistry Research (9NM, AP20), Diagnostics Division, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, IL 60064-6016, USA, Fax: (+1) 847-938-8927

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Donald D. Johnson

Donald D. Johnson

Division Organic Chemistry Research (9NM, AP20), Diagnostics Division, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, IL 60064-6016, USA, Fax: (+1) 847-938-8927

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Rajarathnam E. Reddy

Rajarathnam E. Reddy

Division Organic Chemistry Research (9NM, AP20), Diagnostics Division, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, IL 60064-6016, USA, Fax: (+1) 847-938-8927

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Abstract

The collagen cross-link (+)-deoxypyrrololine (Dpl, 1), a potential biochemical marker for diagnosis of osteoporosis, has been obtained by a general and convergent total synthesis. The key synthetic features involve utilization of a L-glutamic acid derivative as a source for all three chiral centers in (+)-1, and construction of the pyrrole ring by condensation of an α-acetoxynitro compound with benzyl isocyanoacetate.

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