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Tetrahedron Letters

Volumn 22, Issue 8, 1981, Pages 719-722

A diastereoselective route to (±)-isoretronecanol

(2) Flitsch, Wilhelm a Wernsmann, Petra a

a UNIVERSITY OF MÜNSTER (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZIDINE DERIVATIVE; PYRROLIZIDINE DERIVATIVE;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; ISORETRONECANOL; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; THEORETICAL STUDY; TRACHELANTHAMIDINE;

EID: 0019423674 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/0040-4039(81)80132-3 Document Type: Article

Times cited : (33)

References (22)

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2
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3
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10
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- Fuchs¹

11
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- 1H-NMR, MS and correct analytical data.

12
- 84914378224
- The reaction presumably involves nucleophilic ring opening of the cyclopropylphosphonium salt 2 to give a stabilized ylide (see compounds 7), which subsequently undergoes an intramolecular Wittig reaction. As Wittig reactions often are sterically hindered, we first treated 1-carboethoxycyclopentan-2-one with 2 and obtained the expected pentalene derivative.

13
- 84914378223
- 3) δ (ppm) = 171.105 (s), 164.346 (s), 159.472 (s), 101.326 (s), 58.672 (t), 40.020 (t), 32.806 (t), 31.116 (t), 20.263 (t), 13.634 (q).

14
- 84914378222
- (1980) Diplomarbeit. Münster
- Wernsmann¹

15
- 84914378221
- 3) δ (ppm) = 174.290 (s), 171.495 (s), 62.052 (d), 59.542 (t), 44.309 (d), 40.085 (t), 32.741 (t), 29.232 (t), 20.848 (t), 13.114 (q).

16
- 84914378220
- Under the conditions of GLC separation (Carbowax, 12 %, 4 m, 220°C or OV 17, 4 %, 1.7 m, 180°C) the epimerisation of 1c to the thermodynamically more stable exo-isomer 1d cannot be excluded; therefore the amount of 1d herein determined is considered to be the lowest limit.

17
- 0010526485
- The melting point of the picrate (192–194°C, from EtOH) corresponds closely with that reported in the literature (190–192°C). The IR spectrum is in accordance with a published spectrum of an authentic sample
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18
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- 1H-NMR spectrum
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19
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20
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- Thiocarbonyl-Olefinierung, II. Einige präparative Anwendungen der Reaktion vonN-(Thioacyl)urethanen und deren Vinylogen mit resonanzstabilisierten Phosphor-Yliden
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- Gossauer¹ Ernst² Rößlier³ Zilch⁴

21
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- We aimed at the regioselective annelation of substituted monothioimides.

22
- 0019149801
- For a recent synthesis of (−)-isoretronecanol see
- (1980) Tetrahedron Lett. , pp. 3841
- Kraus¹ Neuenschwander²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.