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Synlett

Volumn , Issue 16, 2008, Pages 2443-2446

Stereocontrolled synthesis of the tetracyclic core framework of (-)-lemonomycin

(3) Siengalewicz, Peter a Brecker, Lothar a Mulzer, Johann a

a UNIVERSITY OF VIENNA (Austria)

Author keywords

Acyliminium cyclization; Antitumor antibiotic; Lemonomycin; Pictet Spengler reaction; Tetrahydroisoquinoline

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; LEMONOMYCIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; DESS MARTIN OXIDATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; PICTET SPENGLER REACTION; STEREOCHEMISTRY; STRECKER SYNTHESIS; STRUCTURE ANALYSIS;

EID: 54249145705 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078273 Document Type: Article

Times cited : (12)

References (20)

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10
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- Preparation of aryl bromide 6 was performed via a five-step sequence from 2,6-dimethoxytoluene according to a method developed recently by us
- Preparation of aryl bromide 6 was performed via a five-step sequence from 2,6-dimethoxytoluene according to a method developed recently by us.

11
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- No cyclization product was obtained performing the Pictet-Spengler reaction with the corresponding benzyl-protected phenol
- No cyclization product was obtained performing the Pictet-Spengler reaction with the corresponding benzyl-protected phenol.

12
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14
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- The (E)-(5-bromopent-2-enyl)trimethylsilane side chain employed in the enantioselective Myers' alkylation reaction was prepared by cross-metathesis between allyl-TMS and allyl bromide,
- (a) The (E)-(5-bromopent-2-enyl)trimethylsilane side chain employed in the enantioselective Myers' alkylation reaction was prepared by cross-metathesis between allyl-TMS and allyl bromide,

15
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17
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- Using the unprotected phenol in this reaction sequence led to the undesired formation of the quinone system upon treatment with Dess-Martin periodinane
- Using the unprotected phenol in this reaction sequence led to the undesired formation of the quinone system upon treatment with Dess-Martin periodinane.

18
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19
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- The atom connectivities of all key intermediates were proven by through-bond correlation NMR techniques. In particular the structure of the rigid tetracyclic core in compound 2 was in full agreement with the NOEs and all 1H-1H coupling constants
- 1H coupling constants.

20
- 54249165590
- Synthesis of Tetrahydroisoquinoline 3: Acetic acid (5 μL, 0.078 mmol) and powdered 4 Å molecular sieves were sequentially added to a solution of amino phenol 10 (75 mg, 0.16 mmol) in CH2Cl 2 (2 mL, The resulting solution was degassed by three freeze-pump-thaw cycles. A solution of benzyloxy acetaldehyde 5 (25 μL, 0.171 mmol, 95, in CH2Cl2 (1 mL) was slowly added via a syringe pump to the degassed solution over a period of 8.5 h. After stirring for 20 h at r.t, including the time of the addition, the reaction suspension was filtered through Whatman No. 5 filter paper to remove the molecular sieves. Sat. aq NaHCO3 solution (40 mL) was added to the filtrate and the resulting biphasic solution was extracted with CH 2Cl2 4 x 50 mL, The combined organic phases were dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography
- 3): δ = 7.77 (d, J = 7.6 Hz, 2 H), 7.60 (dd, J = 3.1, 4.3 Hz, 2 H), 7.40 (t, J = 7.5 Hz, 2 H), 7.28-7.35 (m, 2 H + 5 H), 5.42-5.59 (m, 1 H), 5.38 (m, 1 H), 5.02-5.25 (m, 1 H), 4.58 (m, 1 H), 4.27-4.47 (m, 5 H), 4.24 (m, 1 H), 4.09 (m, 1 H), 3.95

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