86197-10-6

Upstream product

• 501665-85-6 cis-5-(methoxymethoxy)-2-penten-1-ol 
• 99165-40-9 3-butenol methoxymethyl ether 
• 107-02-8 acrolein 
• 112596-89-1 (E)-5-hydroxypent-2-enal 
• 107-30-2 chloromethyl methyl ether 
• 501665-82-3 5-hydroxy-(E₃)-3-pentenyl methoxymethyl ether 
• 1159199-45-7 5,5-dimethoxy-(3Z)-pent-3-enyl methoxymethyl ether 
• 86197-09-3 5-methoxymethoxy-2-pentyn-1-ol 
• 5582-60-5 4-(methoxymethyloxy)but-1-yne 

Downstream Products

• 86197-14-0 [(1S,5R,6S)-6-((E)-5-[1,3]Dioxolan-2-yl-3-oxo-pent-1-enyl)-5-(2-methoxymethoxy-ethyl)-cyclohex-2-enyl]-carbamic acid benzyl ester 
• 86258-57-3 [(1R,5R,6S)-6-((E)-5-[1,3]Dioxolan-2-yl-3-oxo-pent-1-enyl)-5-(2-methoxymethoxy-ethyl)-cyclohex-2-enyl]-carbamic acid benzyl ester 
• 163041-87-0 (3E,8Z)-3,8-tetradecadien-1-yl acetate 
• 163041-94-9 (3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate 

Relevant academic research and scientific papers

Enantioselective cascade sequence to indoloquinolizidines and its application in the synthesis of epi-geissochizol

An organocatalyzed one-pot Michael addition and Pictet-Spengler sequence utilizing β-keto amide and aliphatic ,αβ-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-a] quinolizidines as a mixture of keto and enol tautomers. Such tautomeric pairs were transformed into stable compounds with an E-ethylidenyl group in telescoped steps. This method was successfully applied in the synthesis of epi-geissoschizol. Georg Thieme Verlag Stuttgart. New York.

Modular Total Synthesis of iso-Archazolids and Archazologs

Full details on the design, development, and successful implementation of suitable synthetic strategies directed toward the total synthesis of iso-archazolids and archazologs are reported. Both a biomimetic and a multistep total synthesis of iso-archazolid B, the most potent and least abundant archazolid, are described. The bioinspired conversion from archazolid B was realized by a high-yielding 1,8-Diazabicyclo[5.4.0]undec-7-ene catalyzed one-step double-bond shift. A highly stereoselective total synthesis was accomplished in 25 steps, involving a sequence of highly stereoselective aldol reactions, an efficient aldol condensation to forge two elaborate fragments, and a challenging ring-closing metathesis macrocyclization with an unusual Stewart-Grubbs catalyst. These strategies proved to be generally useful and could be successfully implemented for the preparation of three novel iso-archazolids as well as five novel archazologs, lacking the thiazole side chain. A wide variety of further archazolids and archazologs may now be targeted for exploration of the promising anticancer potential of these polyketide macrolides.

PROCESS FOR PREPARING A FORMYLALKENYL ALKOXYMETHYL ETHER COMPOUND AND PROCESSES FOR PREPARING CONJUGATED DIENE COMPOUNDS FROM THE SAME

The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R3CH2OCH2O(CH2)aCH═CHCHO (2), wherein R3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R3CH2OCH2O(CH2)aCH═CHCH(OR1)(OR2) (1), wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, having 2 to 10 carbon atoms; and R3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).

METHOD FOR PREPARING (E3, Z5) -3,5-ALKADIENYL ACETATE

Provided is a method for preparing (E3,Z5)-3,5-alkadienyl acetate and (E3,Z5)-3,5-dodecadienyl acetate which is a sex pheromone of Brazilian apple leafminer. Specifically, provided is a method for preparing (E3,Z5)-3,5-alkadienyl acetate, comprising steps

The "Aqueous" Prins Reaction

(Equation presented) In this communication we demonstrate that Prins cyclization reactions occur under very mild conditions when cyclic α,β-unsaturated acetals are employed as oxocarbenium ion progenitors and allylsilanes are used as nucleophiles. Cycliza

Importance of allylic interactions and stereoelectronic effects in dictating the steric course of the reaction of iminium ions with nucleophiles. An efficient total synthesis of (±) gephyrotoxin

A stereocontrolled total synthesis of (±)-gephyrotoxin in 15 steps and 6.5% overall yield from benzyl trans-1,3-butadiene-1-carbamate is described. A key step is reduction of octahydroquinoline 27 from the more hindered concave α face to provide decahydroquinoline 28. This unusual transformation results from the interplay of allylic (A1,2) steric interactions and stereoelectronic effects.