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Tetrahedron Letters

Volumn 28, Issue 39, 1987, Pages 4569-4572

A stereoselective total synthesis of (9S)-9-dihydroerythronolide A from D-glucose

(5) Tone, Hitoshi a Nishi, Takao a Oikawa, Yuji a Hikota, Masataka a Yonemitsu, Osamu a

a HOKKAIDO UNIVERSITY (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; THEORETICAL STUDY;

EID: 0023259304 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)96566-3 Document Type: Article

Times cited : (68)

References (42)

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11
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- Recently we reported highly stereoselective synthesis of macrolide aglycons such as methynolide, pikronolide, and tylonolide.

13
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15
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16
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17
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- Unless otherwise noted, the numberings are based on that of 3.

18
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- Chiral synthesis of polyketide-derived natural products. Part 4. Synthesis of a left-hand segment with six consecutive chiral centres of dihydroerythronolide A for the total synthesis of erythromycin A from D-glucose
- and alternative synthesis of 6 from propionaldehyde will be reported soon.
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19
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20
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21
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22
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24
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25
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26
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27
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- Protection of 9,11-diol, not of 11,12-diol, as a cyclic acetal is extremely important for the macrolactonization.

28
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29
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30
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- 4 is a 1 : 1 stereoisomeric mixture with regard to the SO position.

31
- 37049093660
- Chiral synthesis of polyketide-derived natural products. Part 5. Synthesis of a chiral segment corresponding to the C-1?C-5 unit of erythromycin A from D-glucose
- and an alternative synthesis of 13 from methallyl alcohol via the Sharpless asymmetric epoxidation will be reported soon.
- (1985) Journal of the Chemical Society, Perkin Transactions 1 , pp. 19
- Oikawa¹ Nishi² Yonemitsu³

32
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33
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- Corey's method (NBS, 2,6-lutidine, 80% MeCN, rt) also gave 5 in 71% yield.

34
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- Corey¹ Erickson²

35
- 84918463596
- Most of excess 4 was recovered (86%). Coupling between 4 and the 6-methylketone derived from 5 gave only poor results in <20% yield.

36
- 84918463595
- 2, in THF, no reaction occurred.

37
- 0000192963
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- Oikawa¹ Yoshioka² Yonemitsu³

38
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39
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- Inanaga¹ Hirata² Saeki³ Katsuki⁴ Yamaguchi⁵

40
- 84918463594
- In this macrolactonization, concentration of DMAP was very important. Yields of 19 in various concentrations of DMAP are as follws [final mM of DMAP (% yield of 19)]: 25 mM (27%); 9.5 mM (14%); 6 mM (13%); 3 mM (0%).

41
- 84918463593
- As pointed out by Stork, an axial methyl group of 9,11-acetonide protection hindered this lactonizition. Actually we, could not obtain 19 by the modified Corey method, and also 20 gave only a trace of lactonization product, which was, however, obtained in 63% yield by highly reactive Yamaguchi's method at high concentration of DMAP.

42
- 84918463592
- 3, 18, 19, and a 6-O-MM derivative of 21 were identical with the respective authentic samples derived from natural erythromycin A in terms of IR, NMR, and MS spectra.

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