534-32-7

Upstream product

• 120595-02-0 (3R,4S,5R)-4-Benzyloxy-5-ethyl-4-methyl-tetrahydro-furan-2,3-diol 
• 64638-70-6 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-hexofuranose 
• 56709-69-4 (E)-(3R,4S,5S,7R,11S,12R)-4-(tert-butyldimethylsilanyloxy)-12-ethyl-3,5,7,11-tetramethyloxacyclododec-9-ene-2,8-dione 
• 127620-05-7 (2R,3S,4S,6R,8E,10S,11R)-10-hydroxy-2,4,6,10-tetramethyl-7-oxo-3-<2-(trimethylsilyl)ethoxymethoxy>-8-tridecen-11-olide 
• 110314-33-5 (E)-(3S,4R,5R,7S,11R,12S)-4-Benzyloxy-12-ethyl-3,5,7-trimethyl-11-(2-oxo-2-phenyl-ethylsulfanyl)-oxacyclododec-8-en-2-one 
• 123488-85-7 [(R)-1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propoxy]-tert-butyl-dimethyl-silane 
• 110314-32-4 (E)-(3S,4R,5R,7S,11R,12S)-4-Benzyloxy-12-ethyl-11-mercapto-3,5,7-trimethyl-oxacyclododec-8-en-2-one 
• 110314-26-6 1-((E)-(2S,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-one 
• 110314-26-6 1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-one 
• 110314-27-7 (R)-1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-thiacycloundec-4-en-2-yl)-propan-1-ol 
• 123538-78-3 (E)-(3R,4S,5S,7R,8S,12R)-4-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-12-ethyl-3,5,7-trimethyl-oxacyclododec-9-ene-2,11-dione 
• 110314-35-7 (4R,7R,8S,9S,11R)-8-Benzyloxy-4-ethyl-7,9,11-trimethyl-5,13-dioxa-bicyclo[10.1.0]tridecane-3,6-dione 
• 110314-29-9 {(R)-1-[(E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-11-(diphenyl-phosphinoyl)-6,8,10-trimethyl-thiacycloundec-4-en-2-yl]-propoxy}-tert-butyl-dimethyl-silane 
• 110314-28-8 [(R)-1-((E)-(2R,6R,8S,9S,10R)-9-Benzyloxy-6,8,10-trimethyl-1-oxo-1λ⁴-thia-cycloundec-4-en-2-yl)-propoxy]-tert-butyl-dimethyl-silane 

Downstream Products

• 69056-12-8 (+)-Prelog-Djerassi lactonic acid 

Relevant academic research and scientific papers

Total synthesis of (+)-methynolide using a Ti-mediated aldol reaction of a lactyl-bearing oxazolidin-2-one, and a vinylogous Mukaiyama aldol reaction

A highly convergent total synthesis of (+)-methynolide, based on two types of stereoselective aldol reaction, was achieved. The C1-C8 and C9-C11 fragments of (+)-methynolide were prepared by a vinylogous Mukaiyama aldol reaction using a vinyl ketene silyl

Total synthesis of methymycin

Methynolide and 10-epi-methynolide were synthesized from the necessary segments, which were prepared by the addition of Grignard reagents to the corresponding α-alkoxyketones utilizing 1,2-stereochemical selection based on Cram chelation control. Ring-clo

Total Synthesis of Methynolide

In this paper the synthesis of methynolide (1), the aglycone of methymycin, a 12-membered macrolide antibiotic is described.We have used the chiral C-1 to C-8 segment 10 which has been combined with the C-9 to C-13 segment 9 to form the carbon skeleton of methynolide.Cyclization of the seco-acid 14 has been accomplished by intramolecular esterification.

Total Synthesis of d,l-Methynolide. Sulfur Removal and Remote Stereocontrol

The details for the conversion of 1 into d,l-methynolide are described.Key steps include the highly selective reduction to alcohol 3, the oxidation α to sulfide sulfur from 3 to thiolactone 13, and the acyl transfer from 14 to the lactone 16.Photochemical

HIGHLY STEREOSELECTIVE SYNTHESIS OF METHYNOLIDE, THE AGLYCONE OF THE 12-MEMBERED RING MACROLIDE METHYMYCIN, FROM D-GLUCOSE

A highly stereoselective and efficient synthesis of methynolide, the aglycone of 12-membered macrolide methymycin, was achieved from of C1-C8 and C9-C13 segments synthesized from D-glucose by employing some stereoselective reactions and benzyl-type protec