A concise and stereoselective total synthesis of L-783,290

Synthesis and Biological Activity of Penaresidins A and B, Penazetidine A, and Related Analogues

“…In 2014, Reddy and co-workers reported a strategy towards penaresidin A ( 1 ) utilizing a convergent approach and combining two fragments, azetidine 215 and sulfone 219 , in a key Julia–Kocienski olefination step (Scheme 35 ). 35 The azetidine core fragment was accessed from commercially available 3,4,6-tri- O -benzyl- d -galactal ( 218 ), which underwent ring-opening via a mercuration-demercuration sequence to form alcohol 217 . A selective amination was applied to allyl alcohol 217 to result in amino alcohol 216 , which preceded azetidine 215 by ring closure.…”

“…The overall synthesis was conducted across 19 steps in 2.1% overall yield from commercially available d -galactal and nonane-1,9-diol. 35…”

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

“…302) [757], dendrodolide A (e.g. 303) [758], dendrodolides A, B, and E [759], L-783,290 [760], 9,10-dihydro ecklonialactone B (includes a late cyclopentenone-forming RCM event) [761], sekothrixide [762], antibiotic A26771B (e.g. 304) [763], approaches to radicicol [764], the cyclocitrinol core (an earlier step employs cross metathesis of a methylenecyclopentane derivative and a 1,5-diene A c c e p t e d M a n u s c r i p t 46 derivative) (e.g.…”

The Application of Dioxygenase‐Based Chemoenzymatic Processes to the Total Synthesis of Natural Products

“…Using related “cutting and stitching” processes we have been able construct a polyoxygenated cyclo‐octane related to the Eastern hemisphere of the structurally remarkable tripartilactam ( 89 ) (Figure ), a target that continues to attract attention but has yet to succumb to total synthesis. By similar means we have also completed total syntheses of both the resorcylic acid lactone L‐783.277 ( 90 ) and its isomer L‐783.290 ( 91 ), the latter having also been prepared in a multi‐step synthesis from d ‐ribose and simplified analogues of the former having been evaluated as kinase inhibitors …”