71325-97-8

Basic information

• Product Name: (4S)-3-[(Z)-Hexadecane-1-ylidene]-4α-hydroxy-5α-methyltetrahydrofuran-2-one
• Synonyms: (-)-Isodihydromahubanolide B;(3Z,4S,5S)-4,5-Dihydro-3-hexadecylidene-4-hydroxy-5-methylfuran-2(3H)-one;(4S)-3-[(Z)-Hexadecane-1-ylidene]-4α-hydroxy-5α-methyltetrahydrofuran-2-one;cis-Dihydromahubanolide B;Dihydromahubanolide B
• CAS NO: 71325-97-8
• Molecular Weight: 0
• Mol File: 71325-97-8.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4S)-3-[(Z)-Hexadecane-1-ylidene]-4α-hydroxy-5α-methyltetrahydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-3-[(Z)-Hexadecane-1-ylidene]-4α-hydroxy-5α-methyltetrahydrofuran-2-one(71325-97-8)
• EPA Substance Registry System: (4S)-3-[(Z)-Hexadecane-1-ylidene]-4α-hydroxy-5α-methyltetrahydrofuran-2-one(71325-97-8)

Safety Data

• Hazardous Substances Data: 71325-97-8(Hazardous Substances Data)

Upstream product

• 132246-25-4 (4S,5S)-3-Hexadec-(Z)-ylidene-4-(4-methoxy-benzyloxy)-5-methyl-dihydro-furan-2-one 
• 78016-95-2 (E)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-octadec-2-enoic acid 
• 78016-95-2 (Z)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-octadec-2-enoic acid 
• 13007-90-4 bis(triphenylphosphine)nickel⁽⁰⁾ dicarbonyl 
• 354579-94-5 (Z)-((E)-2-Propenyl)-octadec-2-enoic acid methyl ester 
• 818-58-6 methyl (E)-pent-3-enoate 
• 629-80-1 n-hexadecylaldehyde 
• 14866-43-4 (1-hexadecyl)triphenylphosphonium bromide 
• 103411-90-1 hexadecanyltriphenylphosphonium iodide 
• 78086-74-5 2-Diazo-1-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-ethanone 
• 78016-91-8 Benzoic acid 2-oxo-2-((4R,5S)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 78016-93-0 (Z)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-octadec-2-en-1-ol 
• 78016-93-0 (E)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-octadec-2-en-1-ol 
• 78016-94-1 (Z)-2-((4S,5S)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-octadec-2-enal 

Relevant articles and documents

Stereopure 1,3-butadiene-2-carboxylates and their conversion into non-racemic α-alkylidenebutyrolactone natural products by asymmetric dihydroxylation

Dienoic esters 1 with the four possible permutations of the C=C configurations were prepared in two steps via non-stereoselective aldol additions followed by stereospecific β-eliminations. Sharpless dihydroxylations of these esters yielded natural and unnatural α-alkylidene-β-hydroxybutyrolactones 2. Among these were synthetic dihydromahubanolide B (cis,Z-2a), isodihydromahubanolide B (cis,E-2a) and, for the first time, litsenolide D1 (ent-trans,Z-2b) and the enantiomer trans,E-2b of litsenolide D2. Competitively, dihydroxyesters 10 were formed.

(Z)-3-alkylidene-4,5-dihydro-4-hydroxy-5-methyl-2-(3H)-furanones by regio- and diastereoselective ene reaction of singlet oxygen (Schenk reaction) with γ-hydroxy vinylstannanes: An enantioselective synthesis of dihydromahubanolide B

(Z)-3-Alkylidene-4,5-dihydro-4-hydroxy-5-methyl-2-(3H)-furanones 5 were prepared from appropriately substituted propargylic alcohols 1 by a sequence of hydromagnesation to γ-hydroxy vinylstannanes 2, subsequent photooxygenation and reduction to stannyl diols 3, iododestannylation to iodo diols 4, and finally cyclization by palladium-catalyzed carbonylation (for 5a) or Ni(CO)2(PPh3)2 (for 5b,c). The reaction sequence can be performed enantioselectively by starting with chiral propargylic alcohols. The current approach constitutes a convenient four-step synthesis of optically active lactones 5 from readily available starting materials and is applied herein to the preparation of the natural lactone dihydromahubanolide B.

SYNTHESIS OF (-)-DIHYDROMAHUBANOLIDE B AND (-)-ISODIHYDROMAHUBANOLIDE B

The total synthesis of (-)-dihydromahubanolide B and (-)-isodihydromahubanolide B isolated from the Amazonian Lauraceae Licaria mahuba (Samp.) Kosterm was achieved starting from (-)-methyl 5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane-4-carboxylate which was readily available from L-(+)-tartaric acid.