Total Synthesis of Tricolorin A

Abstract

Tricolorin A (1), a structurally amazing resin glycoside with promising bioactivities from Ipomoea tricolor cav. (convolvulaceae), was synthesized in a total of 45 steps, with the longest linear sequence of 20 steps and overall yield of 0.65% from D-mannitol. The AB disaccharide 19-membered lactone 2 was constructured by a regioselective macrolactonization using Corey-Nicolaou protocol. The macrolactone tetrasaccharide 33 was realized either by "one-pot two-step" glycosylation procedure or by a stepwise assembly employing the "armed-disarmed" glycosylation strategy.

Synthesis of Anomeric Sulfimides and Their Use as a New Family of Glycosyl Donors

“…Ethyl 2,3‐Di‐ O ‐acetyl‐4,6‐ O ‐benzylidene‐ S ‐( N ‐tosylimino)‐1‐thio‐β‐ D ‐glucopyranoside (5): Preparation from crystalline ethyl 2,3‐di‐ O ‐acetyl‐4,6‐ O ‐benzylidene‐1‐thio‐β‐ D ‐glucopyranoside20 (97 mg, 0.244 mmol) according to Procedure A and purification by column chromatography (petroleum ether/ethyl acetate, 3:7) gave amorphous 5 (127 mg, yield: 92%) in the form of one epimer. [α] D = −177 ( c = 1.0, CHCl 3 ).…”

Crystal Structure of Tricolorin A: Molecular Rationale for the Biological Properties of Resin Glycosides Found in Some Mexican Herbal Remedies

“…Both teams used a macrolactonization approach. [5,6] Fürstner and Müller later used a ring-closing-metathesis strategy to form the macrolactone moiety and succeeded in synthesizing tricolorin A [7] and several other resin glycosides. [8,9] Tricolorin A demonstrates several biological activities of therapeutic interest, such as mammalian cytotoxicity against cultured P-338 and human breast cancer cells, [2] antibacterial activity against Staphyloccocus aureus and Mycobacterium tuberculosis, [1] and antifungal potential correlated to its (1!3)b-d-glucan synthase inhibitory activity.…”

Total synthesis of cleistetroside-2, partially acetylated dodecanyl tetrarhamnoside derivative isolated from Cleistopholis patens and Cleistopholis glauca

“…In Scheme 3: Diol 12 was refluxed with Bu 2 SnO in toluene, 26 followed by reaction with p-methoxybenzyl chloride in the presence of CsF, and Bu 4 NI in DMF (rt) to afford p-tolyl 4-O-acetyl-3-O-PMB-1-thio-a-L Lrhamnopyranoside 17 in a favorable yield (74%). But employing toluene-MeOH as solvent diol 12 was converted to side product 18 due to removal of the acetyl group 27 in C-4-OH.…”