244071-55-4

Upstream product

• 693-25-4 n-pentylmagnesium bromide 
• 37002-45-2 (4S,5S)-2,2-dimethyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolan 
• 98-59-9 p-toluenesulfonyl chloride 
• 172547-16-9 (4S,5S)-(5-n-hexyl-2,2-dimethyl-[1,3]-dioxolan-4-yl)methanol 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 553665-19-3 (4R,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester 

Downstream Products

• 329346-47-6 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3-hydroxy-cyclohex-2-enone 
• 553665-15-9 (4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid (1S,2S)-1-allyl-2-(2-methoxy-ethoxymethoxy)-octyl ester 
• 553665-17-1 (E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one 
• 553664-99-6 Toluene-4-sulfonic acid (2S,3S)-2,3-dihydroxy-nonyl ester 
• 329346-43-2 (4S,5R)-4-Hexyl-5-iodomethyl-2,2-dimethyl-[1,3]dioxolane 

Relevant academic research and scientific papers

Total synthesis of mycestericin A and its 14-epimer

The total synthesis of mycestericin A (1) and its 14-epimer 34 is described herein. The Overman rearrangement of an allylic trichloroacetimidate derived from l-tartrate generated a tetra-substituted carbon with nitrogen and subsequent stereoselective transformations afforded the highly functionalized left-half segment, vinyl iodide. Cross-coupling of the vinyl iodide with a chiral organometallic species synthesized from d-tartrate under the Negishi or Suzuki-Miyaura coupling conditions, followed by deprotection, completed the total synthesis of 1. The 14-epimer of mycestericin A was also synthesized, and a comparison of [α]D values of peracetyl γ-lactone derivatives of mycestericin A and its 14-epimer as well as degradation studies of 1 and 34 fully confirmed the proposed absolute structure of mycestericin A.

Total synthesis of microcarpalide

A total synthesis of the natural product microcarpalide is described. Ring-closing metathesis of a dienic ester was used as the key step. Mannose was used as the chiral pool material for the construction of the olefinic-acid and a Sharpless asymmetric dih

Total synthesis of koninginin D, B and E

Total synthesis of koninginin D, E and B was described. The structures of koninginin B and F, which were deduced as C4 epimer of koninginin E and D, respectively, have been corrected.

First total synthesis of (+)-koninginin D

A total synthesis of (+)-koninginin D (1) is described; the absolute configuration of the immediate antecedent of 1 is shown to have the configuration 7R,9S,10S by X-ray diffraction analysis.