2000
DOI: 10.1039/b002530p
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3-Bromobarekoxide, an unusual diterpene from Laurencia luzonensis

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Cited by 20 publications
(18 citation statements)
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“… 42 , 43 Concerted cyclizations of this fashion have been proposed for other snyderanes. 44 , 45 Although a single enantiomer of TCPT 8 was employed in the cyclization, the production of a racemate convinced us that the level of diastereoselection was substrate rather than catalyst-controlled, and that the ratio of products reflected the thermodynamic preference for the furyl unit to be pseudoaxial, as in 12 , rather than pseudoequatorial as in 13 . The most direct way to probe this hypothesis was to generate the cyclization precursor as a single enantiomer and measure the diastereomeric ratio of the ensuing product mixture.…”
Section: Resultsmentioning
confidence: 99%
“… 42 , 43 Concerted cyclizations of this fashion have been proposed for other snyderanes. 44 , 45 Although a single enantiomer of TCPT 8 was employed in the cyclization, the production of a racemate convinced us that the level of diastereoselection was substrate rather than catalyst-controlled, and that the ratio of products reflected the thermodynamic preference for the furyl unit to be pseudoaxial, as in 12 , rather than pseudoequatorial as in 13 . The most direct way to probe this hypothesis was to generate the cyclization precursor as a single enantiomer and measure the diastereomeric ratio of the ensuing product mixture.…”
Section: Resultsmentioning
confidence: 99%
“…The following Okinawan Laurencia spp. have been investigated to date; L. brongniartii [3,4], L. intricata [5], "L. luzonensis" [6][7][8][9], L. majuscula [10,11], L. mariannensis [11], L. nidifica [11,12], L. venusta [13], L. yonaguniensis [14][15][16] and two undescribed Laurencia species [17,18]. The partially dried alga (133.3 g) collected at Kayo Coast was soaked in MeOH.…”
Section: Previous Studiesmentioning
confidence: 99%
“…(1) those belonging to the α-chamigrene series possessing a trisubstituted double bond between C-7 and C-8 (1-26); (2) those belonging to the β-chamigrene series not designated (246) 5,7-cycloeudesmane (446) aristolane (450)(451)(452)(453)(454)(455)(456)(457)(458)(459)(460)(461)(462)(463) triquinane (490)(491)(492) cedrane (494) 3,6-cyclo-precapnellane (493) aromadendrane (496)(497)(498) africanane (495) calenzanane (500)(501) cyclococane (499) not designated (502) rhodolaurane (508)(509)(510)(511) omphalane (503)(504) not designated (512) gomerane (505)(506)(507) 6,8-cycloeudesmane (447) cyclolaurane (225)(226)(227)(228)(229)(230)…”
Section: Chamigranes and Related Sesquiterpenesmentioning
confidence: 99%