Total Synthesis of the Chlorinated Marine Natural Product Dysamide B.

Durow, Amanda C.; Long, GC; O'Connell, Susan J.; Willis, Christine L.

doi:10.1002/chin.200711167

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2011

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“…Initially, the direct intermolecular lactamization from sulfonamides 4 was investigated as a one-step route to 5 . However, despite similar intramolecular transformations in the literature, , little success was achieved. Efforts were next directed to a two-step hydrolysis/lactamization sequence to produce scaffolds 5 { 1−3 } in good overall yields on multigram scale. , …”

Section: Resultsmentioning

confidence: 99%

Automated Synthesis of a 184-Member Library of Thiadiazepan-1,1-dioxide-4-ones

et al. 2011

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The construction of a 225-member (3 × 5 × 15) library of thiadiazepan-1,1-dioxide-4-ones was performed on a Chemspeed Accelerator (SLT-100) automated parallel synthesis platform, culminating in the successful preparation of 184/225 sultams. Three sultam core scaffolds were prepared based upon the utilization of an aza-Michael reaction on a multifunctional vinyl sulfonamide linchpin. The library exploits peripheral diversity in the form of a sequential, twostep [3 + 2] Huisgen cycloaddition/Pd-catalyzed Suzuki-Miyaura coupling sequence.

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