Knowledge (XXG)

Yaequinolone J1

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An asymmetric total synthesis of yaequinolone J1 has been published in 2018 by V. Vece, S. Jakkepally and S. Hanessian. In 2020, a five-step synthesis of yaequinolone J1 was reported.
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InChI=1S/C27H31NO5/c1-17(2)7-6-15-26(3)16-14-18-8-13-21-22(23(18)33-26)27(30,24(32-5)25(29)28-21)19-9-11-20(31-4)12-10-19/h7-14,16,24,30H,6,15H2,1-5H3,(H,28,29)/t24-,26-,27+/m0/s1
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Vece, V; Jakkepally, S; Hanessian, S (2018). "Total Synthesis and Absolute Stereochemical Assignment of the Insecticidal Metabolites Yaequinolones J1 and J2".
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Uchida, R; Imasato, R; Shiomi, K; Tomoda, H; Omura, S (2005). "Yaequinolones J1 and J2, novel insecticidal antibiotics from Penicillium sp. FKI-2140".
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Except where otherwise noted, data are given for materials in their
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O=C4Nc2c(c1O(/C=C\c1cc2)(C)CC\C=C(/C)C)(O)(c3ccc(OC)cc3)4OC
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Schwan, J; Kleoff, M; Heretsch, P; Christmann, M (2020).
429: 370:"Five-Step Synthesis of Yaequinolones J1 and J2" 124: 449: 8: 456: 442: 99: 15: 281: 169: 144: 151:Key: CPWPNTRWIIAFEG-DOEKTCAHSA-N 7: 410: 408: 115: 428:. You can help Knowledge (XXG) by 268:Total syntheses of yaequinolone J1 14: 412: 205: 199: 22: 236:(at 25 °C , 100 kPa). 208: 193: 1: 387:10.1021/acs.orglett.9b04455 339:10.1021/acs.orglett.8b01701 501: 407: 230: 180: 160: 135: 61: 35: 30: 21: 424:-related article is a 56:-pyranoquinolin-8-one 226: g·mol 18: 240:Infobox references 16: 437: 436: 333:(14): 4277–4280. 303:10.1021/ol052458h 248:Chemical compound 246: 245: 81:Interactive image 492: 485:Antibiotic stubs 458: 451: 444: 416: 409: 399: 398: 365: 359: 358: 321: 315: 314: 286: 225: 210: 207: 201: 195: 188:Chemical formula 128: 117: 103: 83: 26: 19: 17:Yaequinolone J1 500: 499: 495: 494: 493: 491: 490: 489: 465: 464: 463: 462: 405: 403: 402: 367: 366: 362: 323: 322: 318: 288: 287: 283: 278: 270: 252:Yaequinolone J1 249: 242: 237: 223: 213: 204: 198: 190: 176: 173: 168: 167: 156: 153: 152: 149: 143: 142: 131: 118: 106: 86: 73: 57: 12: 11: 5: 498: 496: 488: 487: 482: 477: 467: 466: 461: 460: 453: 446: 438: 435: 434: 420:This systemic 417: 401: 400: 381:(2): 475–479. 360: 316: 297:(25): 5701–4. 280: 279: 277: 274: 269: 266: 247: 244: 243: 238: 234:standard state 231: 228: 227: 221: 215: 214: 211: 202: 196: 191: 186: 183: 182: 178: 177: 175: 174: 171: 163: 162: 161: 158: 157: 155: 154: 150: 147: 146: 138: 137: 136: 133: 132: 130: 129: 121: 119: 111: 108: 107: 105: 104: 96: 94: 88: 87: 85: 84: 76: 74: 67: 64: 63: 59: 58: 39: 33: 32: 28: 27: 13: 10: 9: 6: 4: 3: 2: 497: 486: 483: 481: 478: 476: 473: 472: 470: 459: 454: 452: 447: 445: 440: 439: 433: 431: 427: 423: 418: 415: 411: 406: 396: 392: 388: 384: 380: 377: 376: 371: 364: 361: 356: 352: 348: 344: 340: 336: 332: 329: 328: 320: 317: 312: 308: 304: 300: 296: 292: 285: 282: 275: 273: 267: 265: 263: 262: 257: 253: 241: 235: 229: 222: 220: 217: 216: 192: 189: 185: 184: 179: 170: 166: 159: 145: 141: 134: 127: 123: 122: 120: 114: 110: 109: 102: 98: 97: 95: 93: 90: 89: 82: 78: 77: 75: 71: 66: 65: 60: 55: 51: 47: 43: 38: 34: 29: 25: 20: 430:expanding it 419: 404: 378: 373: 363: 330: 325: 319: 294: 290: 284: 271: 259: 251: 250: 62:Identifiers 53: 49: 45: 41: 480:Penicillium 475:Antibiotics 261:Penicillium 181:Properties 469:Categories 422:antibiotic 375:Org. Lett. 327:Org. Lett. 276:References 256:antibiotic 219:Molar mass 92:ChemSpider 68:3D model ( 37:IUPAC name 395:31909626 355:49710214 347:29975546 311:16321026 291:Org Lett 258:made by 126:11655315 224:449.547 113:PubChem 101:9830053 393:  353:  345:  309:  254:is an 165:SMILES 31:Names 351:S2CID 140:InChI 70:JSmol 426:stub 391:PMID 343:PMID 307:PMID 383:doi 335:doi 299:doi 116:CID 48:,10 471:: 389:. 379:22 372:. 349:. 341:. 331:20 305:. 293:. 264:. 203:31 197:27 44:,9 40:(2 457:e 450:t 443:v 432:. 397:. 385:: 357:. 337:: 313:. 301:: 295:7 212:5 209:O 206:N 200:H 194:C 72:) 54:H 50:R 46:R 42:S

Index


IUPAC name
JSmol
Interactive image
ChemSpider
9830053
PubChem
11655315
InChI
SMILES
Chemical formula
Molar mass
standard state
Infobox references
antibiotic
Penicillium
doi
10.1021/ol052458h
PMID
16321026
Org. Lett.
doi
10.1021/acs.orglett.8b01701
PMID
29975546
S2CID
49710214
"Five-Step Synthesis of Yaequinolones J1 and J2"
Org. Lett.
doi

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