75420-44-9

Upstream product

• 75371-78-7 (R)-3-methyl-4-pentenoic acid 
• 74755-98-9 (6R)-2,6-dimethyloct-7-en-3-one 
• 67-56-1 methanol 
• 64234-27-1 ((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane 
• 220131-44-2 1,1,4-trimethyl-1,2,3,6-tetrahydro-siline 
• 55254-35-8 (R)-3-methyl-dihydro-furan-2-one 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 547-65-9 α-methylene-γ-butyrolactone 
• 20459-97-6 3-Methyl-4-pentensaeure-methylester 
• 75371-77-6 1-oxo-1-phenyl-4(R)-methyl-5-hexene 
• 203315-97-3 (R)-2,2-dimethyl-3-(3-methylpent-4-en-1-yl)oxirane 
• 10281-56-8 (R)-3,7-dimethyl-1,6-octadiene 

Downstream Products

• 30343-72-7 thiobinupharidine 
• 30343-74-9 thionuphlutine B 

Relevant academic research and scientific papers

Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation

We describe a formal synthesis of 10-aza-9-oxakalkitoxin, the hydroxalog of the cytotoxic marine natural product kalkitoxin, that features Mukaiyama Markovnikov silyl peroxidation of a terminal alkene and N-O bond formation as the central enabling steps.

Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly

An asymmetric total synthesis of (+)-6-hydroxythiobinupharidine (1b) and (-)-6-hydroxythionuphlutine (2b), a set of hemiaminal containing dimeric sesquiterpenes isolated from yellow water lilies of the Nuphar genus, is described. The central bis-spirocyclic tetrahydrothiophene ring was forged through the Stevens rearrangement of a sulfonium ylide, generated in situ from the coupling of a copper-carbene with a spirocyclic thietane. This strategy diverges both from the proposed biosynthesis1 and previous syntheses of this family of alkaloids,2,3 all of which employ dimerization of symmetric monomers to form the aforementioned thiaspirane. The coupling of unsymmetrical monomers allowed access to the unsymmetrically oxidized product 2b for the first time.

Total synthesis of (-)-exiguolide via an organosilane-based strategy

An organosilane-based strategy has been used to accomplish the convergent total synthesis of (-)-exiguolide. The key steps involve: (1) geminal bis(silyl) Prins cyclization to construct the A ring; (2) silicon-protected RCM reaction to construct the 20-me

Total Synthesis of (-)-Exiguolide

A concise total synthesis of (-)-exiguolide has been completed in an overall 2.8% yield over 20 steps in the longest linear path. The key strategies involve (1) Prins cyclization/homobromination of dienyl alcohol with the B ring-substituted aldehyde, prep

A ring-closing metathesis approach to cyclic α,β-dehydroamino acids

A comprehensive study on the synthesis and ring-closing metathesis (RCM) of α,β-dehydroamino acids is described. This sequence has led to the formation of a range of biologically relevant functionalized nitrogen heterocycles. The incorporation of chiral b

Silacycles as templates for acyclic diastereoselection

The 4-substituted silacyclohex-3-enes (3) prepared from the vinyl triflate (9) derived from 1,1-dimethyl-1-silacyclohexan-4-one (1) and higher- order organocuprates provides a versatile template for the construction of non-racemic 3-methyl-4-penten-1-ol (6). Through asymmetric hydroboration, 3 affords the requisite β-hydroxysilane (4) with the idea/geometry to undergo elimination to the chiral acyclic silane (5) which is oxidatively converted to 6.

A Stereocontrolled Access to (+/-)-, (-)-, and (+)-Patchouli Alcohol

The racemate and both enantiomers of patchouli alcohol have been synthesized by stereocontrolled routes.The olfactive properties of the alcohols prepared are reported.