Covering: January 2013 to September 2018Sulfur-containing natural products are a large class of significant functional molecules. Many of these compounds exhibit potent biological activities and ...pharmacological properties; in fact, some of them have been developed into important drugs. The total synthesis of sulfur-containing natural products is a subject that has long attracted significant attention from synthetic organic chemists; to achieve this goal, various methods have been developed over the past years. This review surveys total syntheses of sulfur-containing natural products that introduce sulfur atoms using different sulfurization agents to construct related sulfur-containing moieties.
A highly stereoselective total synthesis of Amaryllidaceae alkaloid starting from α-d-galactopyranoside has been described. The salient features of this total synthesis are Ferrier carbocyclization ...reaction for the synthesis of ring A and Suzuki Miyaura coupling of chiral α-iodo enone fragment with aromatic boronic acid followed by modified Bischler-Napieralski cyclization reaction to form the lactam ring.
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Two efficient, metal free reagent systems, PhI(OAc)2-I2 (method A) and IBX-I2 (method B), for stereoselective synthesis of trans-2-deoxy-2-iodoglycosylacetates and O-iodobenzoates respectively from ...differently protected glycals have been developed. They are compatible with a variety of protecting groups and various functional groups at 2C-position. Hexose-3,2-enolone 8 is obtained directly from 2-acetoxy glycal 5 by method A. An application to modified method B has been shown by synthesis of a diastereomerically pure α-glycosyl ortho-hexynylbenzoate 12, a glycosyl donor from 3,4,6-tri-O-acetyl-D-glucal in two steps that has been further utilized in the synthesis of glycosides 13–18.
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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 ..., cross metathesis between chiral fragments 3 and 4 , Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.
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
..., cross metathesis between chiral fragments
3
and
4
, Yamaguchi macrolactonization and selective oxidation of the allylic alcohol are the key features of the synthesis.
A convergent synthesis of macrolide natural product (−)-A26771B starting from
d
-glucal is reported. Key features of this synthesis involve Ferrier rearrangement, cross metathesis of chiral fragments
3
and
4
and Yamaguchi macrolactonization.
