101376-73-2

Upstream product

• 622-08-2 2-Benzyloxyethanol 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 60656-87-3 benzyloxyacetoaldehyde 
• 2605-68-7 methyl 2-(triphenylphosphoranylidene)propionate 
• 26530-60-9 trimethyl 2-phosphonopropionate 
• 100-39-0 benzyl bromide 
• 107905-52-2 ethyl 2-[bis(2,2,2-trifluoroethyl)phosphono]propionate 

Downstream Products

• 70238-41-4 (E)-4-(benzyloxy)-2-methylbut-2-en-1-ol 
• 123269-03-4 thiapsigargin 
• 125496-02-8 (E,E)-7-(Benzyloxy)-6-methyl-1-(triisopropylsilyl)-3,5-heptadien-1-yne 
• 101376-76-5 (E,E)-7-(Benzyloxy)-5-methyl-3,5-heptadien-1-yne 
• 101376-83-4 (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenoic acid methyl ester 
• 101376-80-1 ((6E,8E,10E)-(2R,4R)-5,12-Bis-benzyloxy-2,4,10-trimethyl-dodeca-6,8,10-trienyloxy)-tert-butyl-dimethyl-silane 
• 101376-85-6 (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraenal 
• 101376-84-5 (2E,8E,10E,12E)-(4R,6R)-7,14-Bis-benzyloxy-2,4,6,12-tetramethyl-tetradeca-2,8,10,12-tetraen-1-ol 
• 101376-81-2 (6E,8E,10E)-(2R,4R)-5,12-Bis-benzyloxy-2,4,10-trimethyl-dodeca-6,8,10-trien-1-ol 
• 101376-82-3 (6E,8E,10E)-(2R,4R)-5,12-Bis-benzyloxy-2,4,10-trimethyl-dodeca-6,8,10-trienal 

Relevant academic research and scientific papers

Progress toward the total synthesis of N-methylwelwitindolinone B isothiocyanate

Progress toward the welwitindolinone alkaloid N-methylwelwitindolinone B isothiocyanate is reported. A key reaction to synthesize the [4.3.1] bicycle embedded in the core of the molecule is a furan type 2 intramolecular Diels-Alder reaction with a tetrasubstituted dienophile, which sets the two vicinal quaternary centers present in the natural product. The sterically encumbered cycloaddition precursor was synthesized using a Horner-Wadsworth-Emmons reaction followed by a Suzuki cross-coupling reaction. Finally, introduction of the secondary alkyl chloride was achieved by a regio- and diastereoselective opening of a [2.2.1] oxobicycloheptane functionality.

Stereoselective synthesis of a nonracemic hydronaphthalene subunit of Kijanolide

Lewis acid catalyzed Diels - Alder cyclization of the tetraenal 15 affords the endo product, hydronaphthalene 16, with high diastereoselectivity. Nonracemic 15 is prepared by addition of dienyne 5 to resolved (2S,4S)-5-[(tert -butyldimethylsilyl)oxy]-2,4-

Stereochemistry of SN2' Additions to Acyclic Vinyloxiranes

The isomeric trans-(E)-, trans-(Z)-, cis-(E)-, and cis-(Z)-vinyloxiranes 7,9,17 and 19 were prepared from 2-(benzyloxy)ethanol by sequential Swern-Wittig or Swern-Horner-Emmons propionate condensation, DIBAH reduction, Sharpless epoxidation, Swern oxidation, Wittig or Horner-Emmons acetate condensation, and a second DIBAH reduction.Addition of lithium dimethylcuprate and lithium methylcyanocuprate to these epoxides in THF-eather at -20 to 0 deg C afforded the allylic alcohols 22,25, ent-23, and ent-22 as the major products.These products are formed by anti addition to the lower energy conformer (s-trans for 7,17, and 19 and s-cis for 9) of the respective vinyloxirane.The conformational preferences of transition-state-like geometries of the vinyl-oxiranes, calculated with the aid of Still's MACROMODEL program, were in agreement with the observed trends.

A Stereoselective Synthesis of the Hydronaphthalene Substructure of Kijanolide

The synthesis of a hydronaphthalene substructure of the antitumor antibiotic kijanimicin is described in which four of the seven chiral centers are introduced via a diastereoselective intramolecular Diels-Alder cyclization of an all-(E)-2,8,10,12-tetradec