24587-53-9Relevant articles and documents
1-Octen-3-ol Is Formed from Its Glycoside during Processing of Soybean [ Glycine max (L.) Merr.] Seeds
Matsui, Kenji,Takemoto, Hiroyuki,Koeduka, Takao,Ohnishi, Toshiyuki
, p. 7409 - 7416 (2018)
Soaking and maceration of dry soybean seeds induce the formation of aliphatic volatile compounds that impact the flavor properties of food products prepared from soybean. Most aliphatic volatile compounds are formed through oxygenation of unsaturated fatty acids by lipoxygenases; however, lipoxygenases are not responsible for the formation of 1-octen-3-ol. 1-Octen-3-ol in soybean products is in general an off-flavor compound; thus, a procedure to manage its formation is required. In this study, we show that the formation of 1-octen-3-ol after hydration of soybean seed powder is independent of oxygen, suggesting that 1-octen-3-ol is not formed de novo from unsaturated fatty acids but instead from its derivative. When crude methanol extract of soybean seeds was reacted with β-glycosidases, 1-octen-3-ol was rather liberated from its glycoside. We purified the parent glycoside from soybean seeds and confirmed it as (R)-1-octen-3-yl β-primeveroside [(R)-1-octen-3-yl 6-O-β-d-xylopyranosyl-β-d-glucopyranoside]. Green immature soybean fruits (pericarp and seeds) contain a high amount of 1-octen-3-yl β-primeveroside. Its amount decreases after hydration of dry soybean powder. The results indicate that management of 1-octen-3-ol levels in soybean products requires a different strategy than that applied to off-flavor compounds formed de novo.
A general asymmetric synthesis of (R)-Matsutakeol and flavored analogs
Liu, Jia,Li, Honglian,Zheng, Chao,Lu, Shichao,Guo, Xianru,Yin, Xinming,Na, Risong,Yu, Bin,Wang, Min
, (2017)
An efficient and practical synthetic route toward chiral matsutakeol and analogs was developed by asymmetric addition of terminal alkyne to aldehydes. (R)-matsutakeol and other flavored substances were feasibly synthesized from various alkylaldehydes in high yield (up to 49.5%, in three steps) and excellent enantiomeric excess (up to >99%). The protocols may serve as an alternative asymmetric synthetic method for active small-molecule library of natural fatty acid metabolites and analogs. These chiral allyl alcohols are prepared for food analysis and screening insect attractants.
Sequential Pd(0)-, Rh(I)-, and Ru(II)-catalyzed reactions in a nine-step synthesis of clinprost
Nagy, Emma E.,Hyatt, I. F. Dempsey,Gettys, Kristen E.,Yeazell, Shawn T.,Frempong Jr., Stephen K.,Croatt, Mitchell P.
, p. 586 - 589 (2013)
A step-economical synthesis of clinprost is reported that concludes with 3 different transition metal-catalyzed reactions: Pd-catalyzed decarboxylation with allylic rearrangement, Rh-catalyzed diene-ene [2+2+1] reaction, and Ru-catalyzed cross-metathesis reaction. The complexity bestowed to the molecule from these reactions converts a readily accessible ester to clinprost without using protecting groups in only 9 total steps.
Concise, scalable and enantioselective total synthesis of prostaglandins
Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu
, p. 692 - 697 (2021/06/01)
Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]
Total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α via three-component coupling
Kim, Taehyeong,Lee, Sung Il,Kim, Sejin,Shim, Su Yong,Ryu, Do Hyun
, (2019/09/17)
The asymmetric total synthesis of PGF2α and 6,15-diketo-PGF1α and formal synthesis of 6-keto-PGF1α from a common key intermediate are described. The key intermediate, which has a chiral cyclopentane backbone possessing suitable functional groups with required stereochemistry for both side chains, was prepared from (R)-4-silyloxy-2-cyclopentenone through a three-component coupling reaction. The Wittig reaction, Nozaki-Hiyama-Kishi (NHK) coupling and cross metathesis completed the synthesis of PGF2α, 6,15-diketo-PGF1α and 6-keto-PGF1α.
