This review surveys the total syntheses of sulfur-containing natural products where sulfur atoms are introduced with different sulfurization agents to construct related sulfur-containing moieties.
An efficient total synthesis of 18 membered macrolactone, (+)-Aspicilin (lichen macrolide) has been achieved in 12 linear steps with 10.2% overall yield from carbohydrate based building block D-glucal. Highlights of the strategy include preparation of 2-deoxysugar from protected glycal 14, two-carbon Wittig olefination of the Swern oxidised intermediate 7, union of 'carbohydrate based' fragment 5 and a long chain (C-11) chiral alcohol 6 by Yamaguchi esterification and finally ring closing metathesis of the resulting compound 4.
A convergent total synthesis of a 16-membered macrolactone natural product (-)-A26771B 1 starting from 3,4,6-tri-o-acetyl-D-glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7, HWE olefination to get the fragment 3, cross metathesis between chiral fragments 3 and 4, Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.Abstract: A convergent total synthesis of a 16-membered macrolactone natural product (-)-5 A26771B 1 starting from 3,4,6-tri-o-acetyl-D-glucal 7 is reported. The Ferrier rearrangement of acetylated glucal 7, cross metathesis between chiral frgments 3 and 4, yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.
A copper‐catalyzed highly diastereoselective multicomponent reaction (MCR) of α‐amino aldehydes, dibenzylamine and various alkynes leading to propargyl syn 1,2‐diamines has been established. The methodology has been further supported by the total synthesis of (+)‐ and (−)‐epiquinamides from A3‐coupled adducts derived from l‐ and d‐pipecolic acids, respectively, in overall yields of 31 %.
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