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Tetrahedron Letters

Volumn 34, Issue 37, 1993, Pages 5923-5926

A new approach to asymmetric synthesis of Stork's prostaglandin intermediate

(6) Nakazawa, Makoto a Sakamoto, Yasuharu a Takahashi, Takashi a Tomooka, Katsuhiko a Ishikawa, Katsuya a Nakai, Takeshi a

a TOKYO INSTITUTE OF TECHNOLOGY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PROSTAGLANDIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0027205420 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)73815-9 Document Type: Article

Times cited : (21)

References (25)

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- Stork¹ Isobe²

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- Stork¹ Kraus²

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- Kondo¹ Umemoto² Yako³ Tunemoto⁴

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- in press
- (1993) Natural Product Lett.
- Takahashi¹ Nakazawa² Takatori³ Nishimura⁴ Yamamoto⁵

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- PGs syntheses by using vinylzincates
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- Morita¹ Suzuki² Noyori³

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- 0025630030
- (1990) Tetrahedron Lett. , vol.31 , pp. 7349
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- 0026495525
- (1992) Tetrahedron Lett. , vol.33 , pp. 5973
- Takahashi¹ Shimayama² Miyazawa³ Nakazawa⁴ Yamada⁵ Takatori⁶ Kajiwara⁷

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- Review
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- Nakai¹ Mikami²

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- Review
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- Danishefsky¹ Cabel² Chow³

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19
- 84918719017
- −5 mol/L 243 nm, EtOH; UV 246 nm).

20
- 84918735689
- −4 mol/L, 243 nm, EtOH; UV 244 nm).

21
- 84918745634
- 1, NaH, propargyl bromide, HMPA, 87%; 2) EtMgBr, TMSCl; 3) PPTS, MeOH, 41%; 4) TBSCl, imidazole, 90%.

22
- 33847087437
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7587
- Grieco¹ Takigawa² Bongers³ Tanaka⁴

23
- 0024560436
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- Danishefsky¹ Cabel² Chow³

24
- 84918730581
- Based on the assumption of a thermodynamically controlled process for the Pd(II)-catalyzed allylic acetate rerrangement MM2 calculations on MACROMODEL (ver. 2.5) considering a Boltzman distribution at 67°C suggest that allylic acetates 6 and 7 would exist in a ratio 20 : 80. We are grateful to Professor Clark Still for providing a copy of MACROMODEL (ver. 2.5).

25
- 84918734804
- −5 mol/L, 244 nm, EtOH; UV 244 nm).

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