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Cited by 32 publications
(8 citation statements)
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“…This RCM method proved to be applicable in the construction of spiroketals with six-to eight-membered unsaturated rings with retention of configuration at C1 (Table 4). 34 Grubbs' second-generation catalyst (186; Figure 6) in benzene was more efficient in the formation of larger rings (Table 4, entries 3, 4 and 6). Furthermore, protection of the C2-hydroxyl group is not necessary for the RCM to occur (Table 4, entries 1 and 5) and the reaction also proceeds in the presence of a carbonyl group at C2 (Table 4, 29 but with an additional acetoxy group at C2.…”
Section: Scheme 33mentioning
confidence: 99%
“…This RCM method proved to be applicable in the construction of spiroketals with six-to eight-membered unsaturated rings with retention of configuration at C1 (Table 4). 34 Grubbs' second-generation catalyst (186; Figure 6) in benzene was more efficient in the formation of larger rings (Table 4, entries 3, 4 and 6). Furthermore, protection of the C2-hydroxyl group is not necessary for the RCM to occur (Table 4, entries 1 and 5) and the reaction also proceeds in the presence of a carbonyl group at C2 (Table 4, 29 but with an additional acetoxy group at C2.…”
Section: Scheme 33mentioning
confidence: 99%
“…compounds [30][31][32][33] and more recently, ring closing metathesis reactions of polyalkenes. 34,35 In the present connection, methods that allow the tactical introduction of 2 H into spiroacetals or precursors for clarification of spectroscopic ambiguities or for biosynthetic mapping, are particularly relevant. The strategies of Schwartz and Hayes are in this category but are also of general application.…”
Section: Synthetic Approaches To Spiroacetalsmentioning
confidence: 99%
“…Development of a general paradigm for spiroacetal biosynthesis in Bactrocera sp.The co-occurrence of 1-hydroxynonan-5-one (33) and 6-n-butyl-3,4-dihydro-2H-pyran(34) with spiroacetal 5 in B. cacuminata, and of 2-hydroxyundecan-6-one (51) and 2-methyl-6-n-pentyl-3,4-dihydro-2H-pyran(36) with isomers of 2,8-dimethyl-1,7dioxaspiro[5.5]undecane (4) in B. halfordiae, 45 B. kraussi74 and the giant ichneumon wasp, Megarhyssa nortoni nortoni (Cresson)50,75,76 were the crucial propelling observations in the formulation of our initial hypothesis, with biosynthetically feasible events linking these compounds. Hydration of the pyrans 34 and 36 would provide a mixture of the corresponding pyranol and hydroxyketone (i.e.…”
mentioning
confidence: 99%
“…Hsung and co-workers have used ketal-tethered ring closing metathesis (RCM) for a short total synthesis of an adrena bee pheromone (Scheme 37) [84,85,86]. The synthesis starts with the dihydropyranpyran 164.…”
Section: A Ketal-tethered Rcm Strategy Towards the Synthesis Of Spiroketal Related Natural Products Synthesis Of A Simple Insect Pheromonmentioning
confidence: 99%