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Volumn 35, Issue 43, 1994, Pages 7957-7960

A total synthesis of (-)-reiswigin a via sequential claisen rearrangement-intramolecular ester enolate alkylation

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; DITERPENE; REISWIGIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0028091969 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(94)80021-9 Document Type: Article

Times cited : (16)

References (18)

1
- 0023571259
- Reiswigins A and B, novel antiviral diterpenes from a deepwater sponge
- (1987) Tetrahedron Letters , vol.28 , pp. 5461
- Kashman¹ Hirsh² Koehn³ Cross⁴

2
- 0024334376
- Synthesis of (-)-reiswigin A. Assignment of absolute and relative configuration
- (1989) Tetrahedron Letters , vol.30 , pp. 2465
- Snider¹ Yang²

3
- 0024998522
- Stereo- and enantiospecific syntheses of (-)-Reiswigins A and B. Assignment of absolute and relative configuration
- (1990) The Journal of Organic Chemistry , vol.55 , pp. 4392
- Snider¹ Yang²

4
- 0018238841
- Total synthesis of prostaglandin F2.alpha. by chirality transfer from D-glucose
- For elegant use of an acyclic sequential Claisen rearrangement strategy in natural product synthesis, see:
- (1978) Journal of the American Chemical Society , vol.100 , pp. 8272
- Stork¹ Takahashi² Kawamoto³ Suzuki⁴

5
- 0010317540
- Highly stereoselective intramolecular alkylation of ester enolate: An approach to trans-hydrindane system
- (1986) Tetrahedron Letters , vol.27 , pp. 943
- Ahn¹ Kim² Chun³ Chung⁴

6
- 0027482163
- A stereoselective synthesis of (±)-elemol via an intramolecular SN2′ ester enolate alkylation
- and references cited therein
- (1993) Tetrahedron Letters , vol.34 , pp. 6557
- Kim¹ Lim² Shin³ Kim⁴

7
- 37049086347
- Folding strain control for remote stereocontrol: diastereoselectivity in the ring closure reactions of 2-(6?-trimethylsilylhex-4?-enyl)cyclohex-2-enones with alkyl groups at various positions in the side chain
- and references cited therein
- (1989) Journal of the Chemical Society, Chemical Communications , pp. 1572
- Tokoroyama¹ Okada² Iio³

8
- 0020377228
- Stereospezifische Synthese des Cancerostatikums 5?-Desoxy-5-fluor-uridin (5-DFUR) und seiner 5? -deuterierten Derivate
- (1982) Helvetica Chimica Acta , vol.65 , pp. 1522
- Kiss¹ D'Souza² van Koeveringe³ Arnold⁴

10
- 0000275815
- Anions of protected cyanohydrins as acyl carbanion equivalents and their use in a new synthesis of ketones
- (1971) Journal of the American Chemical Society , vol.93 , pp. 5286
- Stork¹ Maldonado²

11
- 0018637278
- Utility of the Wittig reaction for the construction of side chains of steroids starting from pregnenolone
- (1979) The Journal of Organic Chemistry , vol.44 , pp. 3760
- Schow¹ McMorris²

12
- 0001685085
- Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene
- (1970) Journal of the American Chemical Society , vol.92 , pp. 741
- Johnson¹ Werthermann² Bartlett³ Brocksom⁴ Li⁵ Faulkner⁶ Peterson⁷

13
- 0001544101
- Cycloalkenes by intramolecular wittig reaction
- (1980) Tetrahedron , vol.36 , pp. 1717
- Becker¹

14
- 0000907075
- The Synthesis of Olefins from O,O'-Dialkyl β-Lithioalkylphosphonothioate Esters
- (1966) Journal of the American Chemical Society , vol.88 , pp. 5654
- Corey¹ Kwiatkowski²

15
- 84912990156
- We thank Drs. B. B. Snider (Brandeis University) and F. Koehn (Harbor Branch Oceanographic Institute) for copies of reference spectra of (−)-reiswigin A (1).

16
- 84912970030
- The synthesis was executed as described in order to unambiguously determine the stereoselectivity of the key intramolecular ester enolate alkylation step, although the total number of steps could be reduced in practice to twelve as shown in the following scheme. Selective mono-tosylation of diol 8a, followed by Johnson orthoester Claisen rearrangement on the resulting monotosylate, directly produced cyclization substrate 18. However, cyclization of 18 with KHMDS was accompanied by deprotonation at the allyl ether moiety of the side chain appendage which is of no consequence in the synthesis except being a nuissance in characterization of the products. Full details will be described in due course.

18
- 0014549356
- Albolic acid, a new sesterterpenic acid isolated from insect wax
- (1969) Tetrahedron Letters , pp. 2929
- Rios¹ Gomez²

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