A facile approach to highly functional trisubstituted furans via intramolecular Wittig reactions

Ko-Wei Chen; Siang-en Syu; Yeong-Jiunn Jang; Wenwei Lin

doi:10.1039/c0ob00912a

A facile approach to highly functional trisubstituted furans via intramolecular Wittig reactions

Organic & Biomolecular Chemistry ◽

10.1039/c0ob00912a ◽

2011 ◽

Vol 9 (7) ◽

pp. 2098 ◽

Cited By ~ 35

Author(s):

Ko-Wei Chen ◽

Siang-en Syu ◽

Yeong-Jiunn Jang ◽

Wenwei Lin

Keyword(s):

Wittig Reactions ◽

Trisubstituted Furans

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ChemInform Abstract: A Facile Approach to Highly Functional Trisubstituted Furans via Intramolecular Wittig Reactions.

ChemInform ◽

10.1002/chin.201134096 ◽

2011 ◽

Vol 42 (34) ◽

pp. no-no

Author(s):

Ko-Wei Chen ◽

Siang-en Syu ◽

Yeong-Jiunn Jang ◽

Wenwei Lin

Keyword(s):

Wittig Reactions ◽

Trisubstituted Furans

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ChemInform Abstract: Efficient AgOTf or Ph3PAuCl-AgSbF6Catalyzed Cyclization of 1-Hydroxy-2-alkynylallylphosphonates/2-alkynylallyl Alcohols to 2-Furylphosphonates/2,3,5-Trisubstituted Furans.

ChemInform ◽

10.1002/chin.201246105 ◽

2012 ◽

Vol 43 (46) ◽

pp. no-no

Author(s):

Ramesh Kotikalapudi ◽

K. C. Kumara Swamy

Keyword(s):

Trisubstituted Furans

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Three-Pot Synthesis of Chiral Anti-1,3-diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Epoxidation and Reductive Opening of the Epoxide

Organic Letters ◽

10.1021/acs.orglett.1c01986 ◽

2021 ◽

Author(s):

Yujiro Hayashi ◽

Masashi Tomikawa ◽

Naoki Mori

Keyword(s):

Wittig Reactions

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Synthesis of 8-HEPE and 10-HDoHE in both (R)- and (S)-Forms via Wittig Reactions with COOH-Ylides

Synlett ◽

10.1055/s-0037-1611976 ◽

2019 ◽

Vol 30 (03) ◽

pp. 338-342

Author(s):

Yuta Suganuma ◽

Shun Saito ◽

Yuichi Kobayashi

Keyword(s):

Docosahexaenoic Acid ◽

Eicosapentaenoic Acid ◽

Wittig Reaction ◽

Phosphonium Salt ◽

Wittig Reactions

Wittig reactions using carboxy (CO2H) ylides derived from a carboxylic phosphonium salt and NaN(TMS)2 (NaHMDS) in a 1:1 ratio were applied to the synthesis of 8-HEPE and 10-HDoHE, which are metabolites of eicosapentaenoic acid and docosahexaenoic acid, respectively. The attempted Wittig reaction of 3-(TBS-oxy)pentadeca-4E,6Z,9Z,12Z-tetraenal with the carboxy ylide (2 equiv) derived from Br– Ph3P+(CH2)4CO2H and NaHMDS (1:1) competed with the elimination of the TBS-oxy group at C3 to give a mixture of the Wittig product and the elimination product in 45–50% and 30–40% yields, respectively. The elimination was suppressed completely by using three equiv of the carboxy ylides in THF/HMPA (7–8:1), and the subsequent desilylation gave 8-HEPE in (R)- and (S)-forms. Similarly, both enantiomers of 10-HDoHE were synthesized.

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