(+)-Colletodiol

Schnurrenberger, P.; Hungerbühler, Ernst; Seebàch, Dieter

doi:10.1016/s0040-4039(01)80212-4

Cited by 28 publications

(5 citation statements)

References 14 publications

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“…The third benzoate, 14, was identified as methyl (5S )-5-( pbromobenzoyloxy)hex-2E-enoate by comparison of spectral data including CD, with the enantiomer 15, which was derived from methyl (5R)-5-hydroxyhex-2E-enoate 18,19 prepared from methyl (3R)-3-hydroxybutyrate by a modification of the procedure reported previously. 19,20 This evidence allowed assignment of absolute stereostructure 2 to macrosphelide F.…”

Section: Resultsmentioning

confidence: 89%

“…Methyl (5R)-5-( p-bromobenzoyloxy)hex-2E-enoate, [α] D Ϫ16 (c 0.18 in EtOH), 18,19 was prepared from methyl (3R)-3hydroxyhex-2E-enoate by a modification of the method reported previously. 19,20 To a solution of the ester (7.1 mg) in pyridine (2 cm 3 ) was added p-bromobenzoyl chloride (6 mg), and the reaction mixture was left at room temperature overnight. The mixture was concentrated to dryness under reduced pressure, and the residue was purified by HPLC using MeOHwater (9 : 1) as the eluent to afford methyl (5R)-5-( p-bromobenzoyloxyhex-2E-enoate 15 (5.7…”

Section: Preparation Of Methyl (5r)-5-p-bromobenzoyloxy)hex-2eenoate 15mentioning

confidence: 99%

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Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C, Eâ€“G and I, produced by a Periconia species separated from an Aplysia sea hare

Yamada

Iritani

Doi

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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Macrosphelides E-I have been isolated, along with known macrosphelides A and C, from a strain of Periconia byssoides originally separated from the sea hare Aplysia kurodai, and the absolute stereostructures of macrosphelides E-G and I have been elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and some chemical transformations. In addition, the absolute configuration of macrosphelide C, previously undetermined, has been established by X-ray analysis and application of the modified Mosher method. Macrosphelides E-H inhibited the adhesion of human-leukaemia HL-60 cells to HUVEC.

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Section: Resultsmentioning

confidence: 89%

Section: Preparation Of Methyl (5r)-5-p-bromobenzoyloxy)hex-2eenoate 15mentioning

confidence: 99%

Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C, Eâ€“G and I, produced by a Periconia species separated from an Aplysia sea hare

Yamada

Iritani

Doi

et al. 2001

J. Chem. Soc., Perkin Trans. 1

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“…The required ester 30 eluted first as an oil; (385 mg, 36.8%, 85.2% wrt recovered starting material); vmax/cm-' 1720 and 1655; dH0.O2 (6 H, S, SiCH,), 0.87 (9 H, S, SiCCH,), 1. 13 15.9, 2-H), 5.84 (1 H, m, 2'-H), 6.84 (1 H, dd, J 15.9 and 9.1, 3-H) and 6.95 (1 H, m, 3'-H); m/z (CI, methane) 572 (M', 0.1%), 557 (0.2), 51 1 (I), 475 (3), 413 (6), 359 (8), 337 (25), 271 (59), 212 (45) and 85 (100). This was followed by unreacted alcohol 35 (391 mg, 56.8%).…”

Section: -Methoxyethoxymethy1(2e4r6r)-4-tert-butyldimethylsilox Y Me ...mentioning

confidence: 99%

Enantioselective synthesis of the 13-membered macrodiolide bartanol

O'Neill¹,

Lindell²,

Simpson³

et al. 1996

J. Chem. Soc., Perkin Trans. 1

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The enantioselective synthesis of the unusual 13-membered ring macrodiolide bartanol7 from poly [(R)hydroxybutyrate] is described confirming the 6R,llR,13R configuration of the natural product. The use of a novel ylide 29 with a MEM-ester protecting group is developed to enable a mild, one-pot cleavage of both the acid and alcohol protecting groups in 30 prior to macrocyclisation to the bartanol framework. The outcome of a Wittig chain extension reaction on a mixture of lactols 19 and 22 using this ylide was found to be dependent on the solvent.

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“…As is often the case with highly functionalized substrates, much difficulty was encountered in attempts to efficiently cleave the dithiane. Among the many reagents and conditions screened, including MeI/CaCO 3 , Dess−Martin periodinane, IBX, PIFA, AgNO 3 , Tl(NO 3 ) 3 , Ag(ClO 4 )/NBS, m CPBA/ Ac 2 O/Et 3 N, and HgCl 2 /CaCO 3 , the best yield achieved was 33% using Hg(ClO 4 ) 2 /CaCO 3 25 to give tetraene 4 . Thereafter, the much anticipated IMDA reaction proceeded to give a (1:1) mixture of the desired trans -decalin 3 and a cis -decalin 11 in 77% combined yield.…”

mentioning

confidence: 99%